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  • Digitale Medien  (3.200)
  • 1995-1999  (906)
  • 1935-1939  (946)
  • 1890-1899  (1.348)
  • 1999  (906)
  • 1939  (946)
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  • gene expression  (79)
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  • Digitale Medien  (3.200)
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  • 1995-1999  (906)
  • 1935-1939  (946)
  • 1890-1899  (1.348)
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Schlagwörter
  • 101
    ISSN: 1573-5028
    Schlagwort(e): UV-B ; soybean ; chalcone synthase ; gene expression
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract By developing gene-specific RT-PCR and using filters to allow transmission down to 290 nm (UV-B+) or blocking all radiation below 320 nm (UV-B−), the effect of UV-B+ and UV-B− light on expression of each of the presently known seven members of soybean chalcone synthase (CHS) gene family in dark-grown seedlings was analyzed. Dark expression was detectable already in 18 h dark-germinating embryos, with progressive increases on successive days, suggesting that chs belongs to a class of genes expressed very early during germination, and that the expression at this stage is either constitutive or induced by non-light-dependent factors present in the seed or made available following imbibition. Exposure of 18 h dark-germinating embryos to UV-B− or to UV-B+ light did not lead to an increase in chs signal. However, the 24 h dark-germinating embryos showed a distinct effect of UV-B+, interestingly coinciding with the stage when the head of seedlings was in the process of being pushed up above ground by stem elongation, suggesting the possibility of a developmental switch modulating the appearance of UV-B response. The response to UV-B− was most prominent in chs1 and almost silent in chs2, while the up-regulation by UV-B+ was most prominent in chs5 and chs6 and much less so in chs2. Interestingly, chs2 was noted to be the only member of the Gmchs gene family devoid of H-box, raising the possibility that the H-box may be a good indicator of the photo-inducibility of a chs gene.
    Materialart: Digitale Medien
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  • 102
    ISSN: 1573-5028
    Schlagwort(e): amphidiploid genome structure ; gene expression ; glutamine synthetase ; multigene family ; nitrogen assimilation ; oilseed rape
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract In the amphidiploid genome of oilseed rape (Brassica napus) the diploid ancestral genomes of B. campestris and B. oleracea have been merged. As a result of this crossing event, all gene loci, gene families, or multigene families of the A and C genome types encoding a certain protein are now combined in one plant genome. In the case of the multigene family for glutamine synthetase, the key enzyme of nitrogen assimilation, six different cDNA sequences were isolated from leaf and root specific libraries. One sequence pair (BnGSL1/BnGSL2) was characterized by the presence of amino- terminal transit peptides, a typical feature of all nuclear encoded chloroplast proteins. Two other cDNA pairs (BnGSR1-1/BnGSR1-2 and BnGSR2-1/BnGSR2-2) with very high homology between each other were found in a root specific cDNA library and represent protein subunits for cytosolic glutamine synthetase isoforms. Comparative PCR amplifications of genomic DNA isolated from B. napus, B. campestris and B. oleracea followed by sequence–specific restriction analyses of the PCR products permitted the assignment of the cDNA sequences to either the A genome type (BnGSL1/BnGSR1- 1/BnGSR2-1) or the C genome type (BnGSL2/BnGSR1-2/BnGSR2-2). Consequently, the ancestral GS genes of B. campestris and B. oleracea are expressed simultaneously in oilseed rape. This result was also confirmed by RFLP (restriction fragment length polymorphism) analysis of RT-PCR products. In addition, the different GS genes showed tissue specific expression patterns which are correlated with the state of development of the plant material. Especially for the GS genes encoding the cytosolic GS isoform BnGSR2, a marked increase of expression could be observed after the onset of leaf senescence.
    Materialart: Digitale Medien
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  • 103
    ISSN: 1573-5028
    Schlagwort(e): defense ; gene expression ; leaf senescence ; nitrilase ; pathogen-free ; salicylic acid
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract To determine the range of gene activities associated with leaf senescence, we have identified genes that show preferential transcript accumulation during this developmental stage. The mRNA levels of a diverse array of gene products increases during leaf senescence, including a protease, a ribosomal protein, two cinnamyl alcohol dehydrogenases, a nitrilase and glyoxalase II. Two of the genes identified are known to be pathogen-induced. The senescence specificity of each gene was determined by characterization of transcript accumulation during leaf development and in different tissues. The increased expression of nitrilase in senescent leaves is paralleled by an increase in free indole-3-acetic acid (IAA) levels. Additionally, we have demonstrated that the induction of defense-related genes during leaf senescence is pathogen-independent and that salicylic acid accumulation is not essential for this induction. Our data indicate that the induction of certain genes involved in plant defense responses is a component of the leaf senescence program.
    Materialart: Digitale Medien
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  • 104
    ISSN: 1573-5028
    Schlagwort(e): gene expression ; gibberellin ; H1 histone ; H2B histones ; leaf ; Lycopersicon esculentum
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract After differential screening we isolated cDNA clones encoding a histone H1 (leH1) and three variants of histone H2B (leH2B-1, -2 and -3) from the gibberellin (GA)-deficient mutant of tomato (gib-1). The deduced polypeptide of leH1 is 271 amino acids long and exhibits the typical tripartite structure of histones H1. The full-length cDNA clone leH2B-1 encodes for a protein of 142 amino residues and shows the tripartite organization of histones H2B. The histones leH1 and leH2B, which show no tissue specificity, are developmentally expressed in the leaf. The mRNA accumulation was higher in organs which contain meristematic tissue and/or which have a high proportion of actively cycling cells. In the leaf of the gib-1 mutant we demonstrated GA-enhanced histone leH1 and leH2B expression which was not observed in the wild type. GAs of the early-13-hydroxylated pathway (GA1 and GA3) caused most enhanced transcription compared to GAs of the early-non-hydroxylation pathway (GA4 and GA9). Application of GA to the mutant increased histone expression that could correlate with enhanced DNA replication in leaf tissue. Increased chromosome replication may indicate that there is a higher rate of cell division and/or increase of endopolyploidy which both may be dependent on cell elongation induced by GAs.
    Materialart: Digitale Medien
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  • 105
    Digitale Medien
    Digitale Medien
    Springer
    Plant molecular biology 39 (1999), S. 933-943 
    ISSN: 1573-5028
    Schlagwort(e): cloning ; fruit development ; gene expression ; pea ; polyamine ; spermidine synthase
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Two cDNAs from young pea fruits coding for functional spermidine synthases (EC 2.5.1.16) were isolated. The corresponding genes were named psSPDSYN1 and psSPDSYN2. Both cDNAs complemented spe3Δ gene when introduced into the Y480 strain of Saccharomyces cerevisiae, which is a null mutant for the spermidine synthase gene. psSPDSYN1 and psSPDSYN2 are regulated differentially. psSPDSYN1 is up-regulated early after fruit set whereas psSPDSYN2 is expressed later. Spermidine synthase activity was detected in pea ovaries, and correlates with the pattern of expression of psSPDSYN1. In the pea plant, psSPDSYN1 is highly expressed in actively growing tissues, whereas the highest level of psSPDSYN2 mRNA was detected in fully elongated stem.
    Materialart: Digitale Medien
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  • 106
    ISSN: 1573-5028
    Schlagwort(e): chitin oligomer ; chitinase ; elicitor ; gene expression ; rice ; signal transduction
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Expression patterns of chitinase transcripts induced by N-acetylchitooligosaccharide elicitor were analyzed by northern blot hybridization in order to reveal a signal transduction pathway leading to the activation of class I chitinase genes (Cht-1 and Cht-3), which may play an important role in producing N-acetylchitooligosaccharide elicitor. The transcription level of both genes was enhanced in response to N-acetylchitooligosaccharides larger than pentaose at subnanomolar concentrations. These structure and dose dependencies were consistent not only with those for a 75 kDa high-affinity binding protein for N-acetylchitooligosaccharide elicitor in the plasma membrane, but also with other series of cellular responses including phytoalexin production and the expression of elicitor-responsive genes (EL2, EL3). Therefore, the elicitor signal to evoke these cellular responses including the activation of the chitinase genes could be common and transmitted into cells through the 75 kDa protein. However, the signal transduction pathway for the activation of the chitinase gene appeared to diverge from those for the other elicitor-responsive genes shortly after the signal perception. It was shown that the induction of chitinase expression by N-acetylchitooligosaccharide would require protein phosphorylation, but not de novo protein synthesis. The oxidative burst was demonstrated not to be necessary for transcriptional induction of the all four elicitor-responsive genes (Cht, PAL, EL2, EL3) by N-acetylchitooligosaccharide.
    Materialart: Digitale Medien
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  • 107
    ISSN: 1573-5028
    Schlagwort(e): cytochrome b5 ; fruit and flower development ; gene expression ; in situ hybridisation ; olive
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract We report the characterisation of two cytochrome b5 genes and their spatial and temporal patterns of expression during development in olive, Olea europaea. A PCR-generated probe, based on a tobacco cytochrome b5 sequence, was used to isolate two full-length cDNA clones (cytochrome b5-15 and cytochrome b5-38) from a library derived from 13 WAF olive fruits. The cDNAs encoded proteins of 17.0 and 17.7 kDa, which contained all the characteristic motifs of cytochromes b5 from other organisms and exhibited 63% identity and 85% similarity with each other. The olive cytochrome b5-15 cDNA was then used as a probe for more detailed analysis. Southern blotting revealed a gene family of at least 4–6 members while northern blotting and in situ hybridisation showed a highly specific pattern of gene expression. Very low levels of cytochrome b5 mRNA were detected in tissues characterised by high rates of lipid accumulation, such as young expanding leaves, maturing seeds and ripening mesocarp. The cytochrome b5 genes were not induced at 6 °C and their response to ABA was relatively slow compared with fatty acid desaturase genes. In contrast, high levels of cytochrome b5 gene expression were found in young fruits at the pattern formation (globular/heart) stage of embryogenesis and in vascular and transmitting tissues of male and female reproductive organs. The data are consistent with a major role for cytochrome b5 in developmental processes related to plant reproduction in addition to being an electron donor to microsomal desaturases.
    Materialart: Digitale Medien
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  • 108
    ISSN: 1573-5028
    Schlagwort(e): Amaranthus hypochondriacus) ; gene expression ; trypsin inhibitor
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract We previously isolated and sequenced the major trypsin inhibitor from Amaranthus hypochondriacus seeds. This amaranth trypsin inhibitor (AmTI) is a 69 amino acid protein with high homology to members of the potato-1 inhibitor family. This paper describes the cloning and expression of a cDNA encoding this trypsin inhibitor in various vegetative tissues of the amaranth plant during seed development and imbibition, and investigates the possible induction of AmTI expression by wounding. We obtained a 393 bp cDNA sequence with an open reading frame corresponding to a polypeptide with 76 amino acid residues. With the exception of one residue (Ser-41), the polypeptide agrees with the amino acid sequence previously reported, plus 7 more residues at the N-terminus. These N-terminal residues are thought to be part of the signal used for intracellular sorting. The organ specificity of AmTI gene expression was investigated by northern analysis, showing that mRNA corresponding to AmTI genes was present in stems of plants growing under normal conditions. The kinetics of accumulation of the AmTI-mRNA, protein, and inhibitory activity during seed development and imbibition was determined. AmTI-mRNA accumulation reached a maximum at 14 days after anthesis (daa) and then gradually decreased, being barely detectable 36 daa. The AmTI protein accumulation followed the same profile as the inhibitory activity, both were delayed with respect to the mRNA. The maximum level was observed 22 daa, and then gradually decreased until a steady state was reached as seed maturation proceeded. Upon imbibition, a gradual decrease in AmTI protein and inhibitory activity was shown; however, an AmTI transcript was detected 24 h after imbibition. In contrast to representative members of the potato I family, this inhibitor was not inducible by wounding of leaves.
    Materialart: Digitale Medien
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  • 109
    ISSN: 1573-5028
    Schlagwort(e): embryo ; gene expression ; Glycine max ; oxidoreductase ; seed coat ; testa
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract The soybean Ep gene encodes an anionic peroxidase enzyme that accumulates in large amounts in seed coat tissues. We have isolated a second peroxidase gene, Prx2, that is also highly expressed in developing seed coat tissues. Sequence analysis of Prx2 cDNA indicates that this transcript encodes a cationic peroxidase isozyme that is far removed from Ep in peroxidase phylogeny. To determine the expression patterns for these two peroxidases in developing seeds, the abundance and localization of the Ep and Prx2 transcripts were compared by in situ hybridization. Results show the expression of Ep begins in a small number of cells flanking the vascular bundle in the seed coat, spreads to encircle the seed, and then migrates to the hourglass cells as they develop. Expression of Prx2 occurs throughout development in all cell layers of the seed coat, and is also evident in the pericarp and embryo. Nonetheless, the Ep-encoded enzyme accounts for virtually all of the peroxidase activity detected in mature seed coats. The Prx2 enzyme is either insoluble in a catalytically inactive form, or is subject to degradation during seed maturation.
    Materialart: Digitale Medien
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  • 110
    ISSN: 1573-5028
    Schlagwort(e): ABRE ; embryogenesis ; G-box ; gene expression ; maize ; protein-DNA interaction
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Transcription of the rab28 gene from maize is induced in late embryo development and in response to abscisic acid. We have studied the regulation of the activity of the rab28 promoter in embryos. Two abscisic acid-responsive elements (ABREs) were necessary for expression in embryos of transgenic Arabidopsis and in transient transformation in maize embryos. In vivo footprinting showed that there was protein binding to the ABREs and to other cis elements in the promoter in young embryos before expression of rab28. This shows that the rab28 promoter is in an open chromatin structure before developmental activation. The ABREs are important for the induction and have protein binding in young embryos. Nuclear proteins extracted from embryos before activation of rab28 bound to the ABREs in band shift assays. A complex with different mobility was formed between nuclear proteins and the ABREs after induction of rab28 suggesting a modification of the ABRE-binding factor or an exchange of proteins. The footprints on the ABREs were unaltered by induction with abscisic acid or during developmental activation of rab28. These results indicate that constitutive binding of transcription factor(s) on the ABRE is central in embryonic regulation of the rab28 gene.
    Materialart: Digitale Medien
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  • 111
    ISSN: 1573-5028
    Schlagwort(e): alanine aminotransferase ; gene expression ; GUS expression ; promoter
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract A cDNA clone encoding alanine aminotransferase (AlaAT) has isolated from randomly sequenced clones derived from a cDNA library of maturing rice seeds by comparison to previously identified genes. The deduced amino acid sequence was 88% and 91% homologous to those of the enzymes from barley and broomcorn millet (Panicum miliaceum), respectively. Using this cDNA as a probe, we isolated and sequenced the corresponding genomic clone. Comparison of the sequences of the cDNA and the genomic gene revealed that the coding region of the gene was interrupted by 14 introns 66 to 1547 bp long. Northern and western blotting analyses showed that the gene was expressed at high levels in developing seeds. When the 5′-flanking region between −930 and +85 from the site of initiation of transcription was fused to a reporter gene for β-glucuronidase (GUS) and then introduced into the rice genome, histochemical staining revealed strong GUS activity in the inner endosperm tissue of developing seeds and weak activity in root tips. Similar tissue-specific expression was also detected by in situ hybridization. These results suggest that AlaAT is involved in nitrogen metabolism during the maturation of rice seed.
    Materialart: Digitale Medien
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  • 112
    Digitale Medien
    Digitale Medien
    Springer
    Plant molecular biology 39 (1999), S. 161-169 
    ISSN: 1573-5028
    Schlagwort(e): expansin ; fruit growth ; fruit softening ; gene expression ; Lycopersicon esculentum
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract cDNA clones encoding homologues of expansins, a class of cell wall proteins involved in cell wall modification, were isolated from various stages of growing and ripening fruit of tomato (Lycopersicon esculentum). cDNAs derived from five unique expansin genes were obtained, termed tomato Exp3 to Exp7, in addition to the previously described ripening-specific tomato Exp1 (Rose et al. (1997) Proc Natl Acad Sci USA 94: 5955–5960). Deduced amino acid sequences of tomato Exp1, Exp4 and Exp6 were highly related, whereas Exp3, Exp5 and Exp7 were more divergent. Each of the five expansin genes showed a different and characteristic pattern of mRNA expression. mRNA of Exp3 was present throughout fruit growth and ripening, with highest accumulation in green expanding and maturing fruit, and lower, declining levels during ripening. Exp4 mRNA was present only in green expanding fruit, whereas Exp5 mRNA was present in expanding fruit but had highest levels in full-size maturing green fruit and declined during the early stages of ripening. mRNAs from each of these genes were also detected in leaves, stems and flowers but not in roots. Exp6 and Exp7 mRNAs were present at much lower levels than mRNAs of the other expansin genes, and were detected only in expanding or mature green fruit. The results indicate the presence of a large and complex expansin gene family in tomato, and suggest that while the expression of several expansin genes may contribute to green fruit development, only Exp1 mRNA is present at high levels during fruit ripening.
    Materialart: Digitale Medien
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  • 113
    ISSN: 1573-5028
    Schlagwort(e): cDNA cloning ; fruit ripening ; gene expression ; non-climacteric fruit ; wild strawberry (Fragaria vesca L.)
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Wild strawberry (Fragaria vesca L.) is an attactive model system for studying ripening in non-climacteric fruit, because of its small diploid genome, its short reproductive cycle, and its capacity for transformation. We have isolated eight ripening-induced cDNAs from this species after differential screening of a cDNA library. The predicted polypeptides of seven of the clones exhibit similarity to database protein sequences, including acyl carrier protein, caffeoyl- CoA 3-O-methyltransferase, sesquiterpene cyclase, major latex protein, cystathionine γ-synthase, dehydrin and an auxin- induced gene. A ninth cDNA clone that was constitutively expressed is predicted to encode a metallothionein-like protein. None of these proteins appear to be directly related to events generally associated with ripening such as cell wall metabolism or the accumulation of sugars and pigments, rather, their putative functions are indicative of the wide range of processes upregulated during fruit ripening.
    Materialart: Digitale Medien
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  • 114
    ISSN: 1573-5028
    Schlagwort(e): cowpea (Vigna unguiculata L.) ; drought ; gene expression ; lipid degradation ; phospholipase D
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Phospholipase D, a major lipid-degrading enzyme in plants, was studied in two cultivars of Vigna unguiculata L.Walp, differing in their tolerance to drought (cv. EPACE-1, drought-tolerant, and cv. 1183, drought-susceptible). Enzymatic activities, measured with 14C-PC as substrate, increased when plants were submitted to water stress, the increase being much higher in the drought-sensitive cultivar. A 2911 bp cDNA encoding a putative phospholipase D (VuPLD1) was isolated from a cDNA library prepared from V. unguiculata leaves. The deduced amino acid sequence (809 residues) shows 85.5% identity and 91.3% similarity to that of PLD from Ricinus communis. The expression of the VuPLD1 gene in the leaves is differently modulated by water deficit, depending on the intensity of stress and the tolerance or sensitivity of the plants. In the drought-susceptible V. unguiculata cv. 1183, it readily increased under water stress, reaching maximum values at mild water deficit (−1.5 MPa). In the drought-tolerant cv. EPACE-1, VuPLD1 mRNA remained low throughout the whole drought treatment. Dehydration of leaves led to a dramatic increase in transcript level in both cultivars. Changes in protein amounts semi-quantified by immunoblotting correlated well with variations in transcript steady-state level. Taken together, these results showed that phospholipase D in cowpea plants is essentially regulated at the transcriptional level, and that gene expression is strongly stimulated even by moderate water deficit in the drought-sensitive plant. On the contrary, the drought-tolerant plant presents a remarkable stability of PLD gene expression in conditions of water stress.
    Materialart: Digitale Medien
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  • 115
    ISSN: 1573-5028
    Schlagwort(e): reproductive development ; gene expression ; subtractive hybridization ; cauliflower
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Using the meristems of the cauliflower curd as a source of tissue and a series of subtractive hybridizations and amplification reactions, we have constructed a cDNA library highly enriched in cDNAs expressed in reproductive meristems. The analysis of a sample of 250 clones from this library identified 22 cDNA clones corresponding to genes specifically expressed in these cauliflower meristems. Apart from two clones that corresponded to APETALA1, and two other ones showing similarity to different aminoacyl-tRNA synthetases, the remaining clones showed no similarity to any sequence in the databases and may correspond to novel genes. One of these clones, BoREM1, was further characterized and found to correspond to a gene encoding a protein with features of regulatory proteins that follows a expression pattern very similar to the LEAFY transcripts.
    Materialart: Digitale Medien
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  • 116
    ISSN: 1573-5028
    Schlagwort(e): ammonium ; gene expression ; glutamine synthetase ; nodules ; positive element ; promoter
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract In order to identify important promoter elements controlling the ammonium-regulated expression of the soybean gene GS15 encoding cytosolic glutamine synthetase, a series of 5′ promoter deletions were fused to the GUS reporter gene. To allow the detection of positive and negative regulatory elements, a series of 3′ deletions were fused to a −90 CaMV 35S promoter fragment placed upstream of the GUS gene. Both types of construct were introduced into Lotus corniculatus plants and soybean roots via Agrobacterium rhizogenes-mediated transformation. Both spectrophotometric enzymatic analysis and histochemical localization of GUS activity in roots, root nodules and shoots of transgenic plants revealed that a strong constitutive positive element (SCPE) of 400 bp, located in the promoter distal region is indispensable for the ammonium- regulated expression of GS15. Interestingly, this SCPE was able to direct constitutive expression in both a legume and non- legume background to a level similar to that driven by the CaMV 35S full-length promoter. In addition, results showed that separate proximal elements, located in the first 727 bp relative to the transcription start site, are essential for root- and root nodule-specific expression. This proximal region contains an AAAGAT and two TATTTAT consensus sequences characteristic of nodulin or nodule-enhanced gene promoters. A putative silencer region containing the same TATTTAT consensus sequence was identified between the SCPE and the organ-specific elements. The presence of positive, negative and organ-specific elements together with the three TATTTAT consensus sequences within the promoter strongly suggest that these multiple promoter fragments act in a cooperative manner, depending on the spatial conformation of the DNA for trans-acting factor accessibility.
    Materialart: Digitale Medien
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  • 117
    ISSN: 1573-5028
    Schlagwort(e): embryo-abundant cDNAs ; gene expression ; gymnosperm ; Picea glauca ; somatic embryogenesis
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Six somatic embryogenesis-associated cDNAs (PgEMB2, 6, 7, 8, 24 and 34) from white spruce (Picea glauca (Moench) Voss) somatic embryos have been characterized. Transcript accumulation during somatic embryo development and subsequent germination related to these genes, indicated that they were developmentally regulated. The transcripts related to clones PgEMB2, 6, 24 and 34 were also detected during zygotic embryo development, but transcripts of clones PgEMB7 and 8 were not. PgEMB24 had a similar gene expression pattern to spruce Em-like late embryo abundant (lea) gene, but other clones had no similarities in gene expression to either spruce lea-like or storage protein genes. Abscisic acid, a stimulator for spruce somatic embryo maturation, did not obviously affect gene expression corresponding to these cDNAs. The predicted proteins are distinguishable from known LEA proteins based on analyses of hydropathy plots, amino acid compositions and deduced protein structures. The similarities of the spruce cDNAs, and protein sequences predicted from these cDNAs, to other sequence data are described.
    Materialart: Digitale Medien
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  • 118
    ISSN: 1573-5028
    Schlagwort(e): gene expression ; GT-1 ; PR-1a ; PR proteins ; salicylic acid-induced ; transcription factors
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Infection of Nicotiana tabacum Samsun NN with tobacco mosaic virus (TMV) results in a hypersensitive plant response and leads to systemic acquired resistance (SAR). The induction of SAR is mediated by the plant hormone salicylic acid (SA) and is accompanied by the induced expression of a number of genes including the pathogenesis-related (PR) gene 1a. Previously, it has been found that TMV infection and SA treatment resulted in a reduction of binding of nuclear protein GT-1 to far-upstream regions (−902 to −656) of the PR-1a gene. To test if GT-1 is a negative regulator of PR-1a gene expression, the effects of mutations in the seven putative GT-1 binding sites in this region were studied in vitro using dimethyl sulfate interference footprinting and band shift assays. This showed that at least one of the seven sites is indeed a GT-1 binding site. However, when tested in transgenic plants, the mutations did not result in constitutive expression of the chimeric PR-1a/GUS transgene, while inducible expression after SA treatment was decreased. The results suggest that binding of GT-1-like proteins to far-upstream PR-1a promoter regions indeed influences gene expression. A possible model for GT-1's mode of action in PR-1a gene expression is discussed.
    Materialart: Digitale Medien
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  • 119
    Digitale Medien
    Digitale Medien
    Springer
    Plant molecular biology 40 (1999), S. 985-995 
    ISSN: 1573-5028
    Schlagwort(e): aquaporin ; gene expression ; growth ; Oryza sativa ; plasma membrane intrinsic protein (PIP) ; rice
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Membrane intrinsic proteins facilitate movement of small molecules often times functioning as water channels. We have identified two genes from rice which encode proteins with characteristic features of plasma membrane intrinsic proteins (PIP). They possess six membrane-spanning domains, an NPA repeat, overall high sequence homologies and characteristic C- and N-terminal hallmark motifs which allowed assignment of OsPIP1a to the PIP1 subfamily and of OsPIP2a to the PIP2 subfamily. OsPIP1a and OsPIP2a showed similar but not identical expression patterns. The two genes were expressed at higher levels in seedlings than in adult plants and expression in the primary root was regulated by light. In internodes of deepwater rice plants which were induced to grow rapidly by submergence, transcript levels were slightly induced in the intercalary meristem (IM) and slightly reduced in the elongation zone (EZ) after 18 h. In internodes of GA-induced excised stem sections transcript levels transiently declined in the IM and EZ after 1 h and subsequently recovered to elevated levels after 18 h. GA also induced OsPIP expression in non-growing tissue after 18 h. In the IM of submergence-induced stem sections transcript levels remained constitutive. The different growth-promoting treatments showed no direct correlation between growth rate and OsPIP gene expression in dividing or expanding cells. In fact, treatment of excised stem sections with ABA or drought stress induced similar changes in OsPIP expression in the growing zone during the first 6 h as GA did. We conclude that regulation of OsPIP1a and OsPIP2a expression is not primarily controlled by growth. GA-induced growth may however change the water status of cells which in turn results in altered PIP abundance.
    Materialart: Digitale Medien
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  • 120
    ISSN: 1573-5028
    Schlagwort(e): ACC synthase ; chilling ; Citrus sinensis ; ethylene ; gene expression ; peel
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Diurnal change in the temperature below or above 12.5 °C hastens the degreening of citrus peel and elicits the phytohormone ethylene production in citrus fruit. Ethylene triggers the degradation of chlorophyll and synthesis of carotenoids in citrus peel. To investigate if ethylene is required for the degreening of citrus peel elicited by low temperatures, we studied the chilling-regulated gene expression of ACC synthase, one of the key enzymes catalyzing ethylene biosynthesis. We isolated and characterized a chilling-inducible 1-aminocyclopropane-1-carboxylate synthase (ACC synthase) gene, CS-ACS1, and a chilling-repressible gene, CS-ACS2, from citrus peel. The CS-ACS1 transcript 1.7 kb in length encodes a polypeptide of 483 amino acids (M r 54 115, pI 6.63), whereas the CS-ACS2 transcript of 1.8 kb encodes a polypeptide of 477 amino acids (M r 53 291, pI 6.72). Both genes showed a rapid but transient induction (within 2.4 h) of transcripts upon rewarming after the chilling (4 °C) treatment. After 24 h of incubation at room temperature, CS-ACS1 mRNA diminished to an undetectable level, whereas the CS-ACS2 mRNA regained its basal level of expression attained prior to the chilling treatment. Chilling-induced ethylene production and ACC accumulation were also observed upon rewarming. Both genes were also induced by the wound stress (excision). The protein synthesis inhibitor cycloheximide super-enhances the accumulation of both ACS transcripts at room temperature. Molecular analysis of the 3.3 kb genomic DNA of CS-ACS1 revealed that this gene consists of three introns and four exons. The intron 3 is exceptionally large (1.2 kb) and shares significant homology with mitochondrial DNA, supporting the intron-late theory.
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  • 121
    Digitale Medien
    Digitale Medien
    Springer
    Plant molecular biology 41 (1999), S. 351-361 
    ISSN: 1573-5028
    Schlagwort(e): chromatin ; gene expression ; high-mobility-group protein HMG1 ; HMGe ; protein stability ; Zea mays
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract The nuclear HMG1 proteins of higher plants are small non-histone proteins that have DNA-bending activity and are considered architectural factors in chromatin. The occurrence of the chromosomal HMG1 proteins, HMGa, HMGc1/2 and HMGd, in various maize tissues was analyzed, and in the course of these studies a novel HMG1 protein, now termed HMGe, was identified. Purification and characterization of HMGe (Mr 13 655) and cloning of the corresponding cDNA revealed that it displays only moderate similarity to other members of the plant HMG1 protein family. The five maize HMG1 proteins could be detected in kernels, leaves, roots and suspension culture cells, indicating that these proteins can be expressed simultaneously and occur relatively ubiquitously. However, the various HMG1 proteins are present in significantly different quantities with HMGa and HMGc1/2 being the most abundant HMG1 proteins in all tissues tested. Furthermore, the relative amounts of the various HMG1 proteins differ among the tissues examined. The HMG1 proteins were found to be relatively stable proteins in vivo, with HMGc1/2, HMGd and HMGe having a half-life of ca. 50 h in cultured cells, while the half-life of the HMGa protein is ca. 65 h. Collectively, these findings are compatible with the concept that the different plant HMG1 proteins might act as general architectural proteins in concert with site-specific factors in the assembly of certain nucleoprotein structures involved in various biological processes.
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  • 122
    ISSN: 1573-5028
    Schlagwort(e): alkaloids ; gene expression ; Nicotiana tabacum ; nicotine ; putrescine N-methyltransferase ; tobacco gene evolution
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract The structure and nuclear genomic organization of the gene family encoding putrescine N-methyltransferase (PMT), the key enzyme in diverting polyamine metabolism towards the biosynthesis of nicotine and related alkaloids, was examined in Nicotiana tabacum. Five genes encoding PMT are present in the N. tabacum genome and all are expressed. The complete coding region and immediate 5′- and 3′- flanking regions were characterized for four members of the gene family and the Exon 1 region of the fifth member of the family was determined. Comparison of the nucleotide and deduced amino acid sequences of the N. tabacum PMT genes with those of presumed progenitor species, N. sylvestris, N. tomentosiformis and N. otophora, revealed that three members of the N. tabacum PMT gene family were most similar to the three genes present in N. sylvestris, whereas the two remaining PMT genes were similar to PMT genes present in N. tomentosiformis and N. otophora genomes, respectively. These data are consistent with an evolutionary origin of N. tabacum resulting from a cross involving N. sylvestris and an introgressed hybrid between N. tomentosiformis and N. otophora. The five PMT genes present in N. tabacum are expressed in the roots of wild-type plants, but not in other organs. The steady-state level of all five PMT transcripts is transiently increased in roots following topping (removal of the floral meristem), although the maximum level of induction for the individual transcripts varies considerably. In contrast to wild-type plants, no increase in PMT transcript levels was observed in a low-alkaloid (nic1nic2) mutant of Burley 21. These data support a role for nic1 and nic2 in the global regulation of alkaloid formation in tobacco and provide for the first time molecular confirmation of the presumed origin of cultivated tobacco.
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  • 123
    Digitale Medien
    Digitale Medien
    Springer
    Plant molecular biology 41 (1999), S. 425-433 
    ISSN: 1573-5028
    Schlagwort(e): D1 protein ; gene expression ; psbA genes ; redox regulation ; Synechococcus
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Three psbA genes encode two different forms of the photosystem II reaction centre protein D1 in Synechococcus sp. PCC 7942. The psbAI gene encoding D1 protein form I (D1:1) is mainly expressed under low growth light conditions while the psbAII and psbAIII genes, encoding D1 protein form II (D1:2), are induced under stress conditions (e.g. high light or low temperature). In this paper we show that psbAII/III genes can be rapidly induced even under low growth light conditions by adding the thiol reductant (DTTred) to Synechococcus cell culture, at a concentration that does not affect cell growth or photosynthetic activity. Similar induction of psbAII/III genes was obtained by illuminating the cells with photosystem I light. In both instances psbAI gene down-regulation coincided with the up-regulation of psbAII/III genes. DTTred-induced exchange in transcript pools was subsequently followed by an exchange of D1:1 for D1:2 at the protein level. Thiol oxidants, iodosobenzoic acid or diamide, reverted the effects of DTTred on psbA gene expression. Thiol oxidants and the thiol-modifying agent N-ethylmaleimide also totally prevented high-light induction of psbAII/III genes. These data strongly suggest that the up-regulation of psbAII/III genes that occurs under stress conditions is mediated by production of thiol reductants, whereas the expression of the psbAI gene is sustained by the more oxidizing conditions that prevail during the steady-state growth of cells.
    Materialart: Digitale Medien
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  • 124
    ISSN: 1573-5036
    Schlagwort(e): ammonium assimilation ; Amanita muscaria ; carbon allocation ; ectomycorrhiza ; gene expression ; Picea abies ; sugar transport
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Land- und Forstwirtschaft, Gartenbau, Fischereiwirtschaft, Hauswirtschaft
    Notizen: Abstract The symbiosis (ectomycorrhiza, ECM) between roots of trees and shrubs of boreal and temperate forest ecosystems and soil fungi is essential for water and nutrient acquisition of the plants. The functionality of ECM is largely dependent on the ability of the host plant to supply photoassimilates to the fungus via the symbiotic interface. Based on sterile in vitro and non-sterile pot experiments, we review data which gives evidence that hexoses are supplied to the fungus by the host plant (mainly glucose and fructose), and that these sugars, at least in part, control development and function of ECM by interfering with fungal gene expression. We further show that any factor which reduces hexose allocation to the host–fungus interface will adversely affect ECM development. As an example, we address the impact of increased supply of nitrogen on the biochemistry of plant–fungus interaction and discuss potential consequences on host performance.
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  • 125
    Digitale Medien
    Digitale Medien
    Springer
    Plant molecular biology 41 (1999), S. 301-311 
    ISSN: 1573-5028
    Schlagwort(e): bundle sheath cell ; C4 photosynthesis ; gene expression ; PEP carboxykinase ; prokaryotic expression ; Zea mays
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract We isolated a full-length cDNA that encodes ATP-dependent phosphoenolpyruvate carboxykinase (EC 4.1.1.49, PCK) from leaves of maize, an NADP-malic enzyme type C4 plant. The mRNA was specifically and rather abundantly expressed in bundle sheath cells in accordance with the recent finding of cell-type-specific localization of PCK protein in maize, which has been detected with antibodies against cucumber PCK protein. The predicted protein had an N-terminal extension, which is characteristic of plant PCKs. The transcript level was much higher in the daytime than at night in 14-day old seedlings. However, in 42-day old plants the extent of diurnal change decreased. The maize PCK was expressed in Escherichia coli with the pET32 plasmid and purified to homogeneity. Through digestion with enterokinase, two types of enzyme were prepared; one with an intact N-terminus and the other lacking its N-terminal 77 amino acid residues due to over-digestion. The truncated protein had about 2-fold higher specific activity than the intact one, and was inhibited by 3-phosphoglycerate (3-PGA) with an I0.5 of 17.5 mM. In contrast, the intact protein was almost insensitive to 3-PGA. These results strongly suggest that the intact N-terminal extension may be involved in the regulation of PCK activity in vivo through some modification such as reversible phosphorylation.
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  • 126
    ISSN: 1573-5028
    Schlagwort(e): calcium-dependent protein kinase ; gene expression ; immunoassays ; light regulation ; rice ; seed development
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract We investigated the spatial and temporal expression patterns of two rice calcium-dependent protein kinases (CDPKs), OsCDPK2 and OSCDPK11, using isoform-specific antisera. Bands of the expected molecular sizes for OsCDPK2 (59 kDa) and OsCDPK11 (61 kDa) were detected on western blots. OsCDPK2 and OsCDPK11 mRNA and protein levels increased in unison during flower development. However, at the onset of seed development, the protein expression profiles diverged significantly. OsCDPK2 protein was expressed at low levels during early seed development, but increased to high levels that were maintained in later stages (20 days after fertilisation, DAF). Conversely, OsCDPK11 protein levels were high at the beginning of seed development, but fell rapidly from 10 DAF onwards. This decrease in the level of OsCDPK11 protein was associated with the abundant synthesis of a truncated mRNA species. OsCDPK2 expression was also closely associated with light perception. OsCDPK2 protein was barely detectable in green leaves exposed to light, but levels increased sharply when plants were shifted to darkness. Initially, this increase reflected a rapid elevation in the levels of OsCDPK2 mRNA, which was normally located in the mesophyll. Conversely, OsCDPK11 mRNA and protein levels were unaffected by light. These data strongly indicate that two rice CDPK isoforms have different functions in seed development and in response to light in leaves.
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  • 127
    Digitale Medien
    Digitale Medien
    Springer
    Euphytica 106 (1999), S. 117-123 
    ISSN: 1573-5060
    Schlagwort(e): differential display ; gene expression ; heterosis ; hybrid wheat ; seedling leaf
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Land- und Forstwirtschaft, Gartenbau, Fischereiwirtschaft, Hauswirtschaft
    Notizen: Abstract Differential display of mRNA was used to analyze the differences of gene expression in seedling leaves between heterotic hybrid/nonheterotic hybrid and their parental inbreds in order to study the molecular basis of heterosis in wheat. The results indicated that patterns of gene expression in hybrids differ significantly from their parents. Both quantitative and qualitative differences were observed. The quantitative differences include gene over-expression, gene under-expression in hybrid and dominant expression of highly-expressed parental genes in hybrids. The qualitative differences include silencing in hybrids of genes expressed either in male or female parent, and silencing in hybrids of genes expressed in both parents. Expression in hybrid of genes only expressed either in male or female parent was also observed. It was also found that some genes expressed at high level in heterotic hybrid were underexpressed or expressed at low level in nonheterotic hybrid. One differentially expressed cDNA fragment 4B was cloned and sequenced after being confirmed through Northern blot analysis. Homology search in GenBank proved that the cDNA fragment is a new sequence. The selection of primers for differential RNA display in wheat and the relationship between wheat heterosis and alteration of gene expression in hybrids as compared to their parental inbreds were also discussed.
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  • 128
    Digitale Medien
    Digitale Medien
    Springer
    Plant growth regulation 29 (1999), S. 47-76 
    ISSN: 1573-5087
    Schlagwort(e): cold ; chill ; freezing ; gene expression ; signal transduction pathways
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Land- und Forstwirtschaft, Gartenbau, Fischereiwirtschaft, Hauswirtschaft
    Notizen: Abstract Temperature is expected to affect all plant processes. Consistent with this, expression of a large number of specific mRNAs and proteins is up-regulated during cold-acclimation. Their possible functions are outlined, encompassing a wide range of processes, some possibly related to other winter stresses besides cold. Some of the cold-responsive sequences are associated with constitutive or stress-related metabolism, others are probably protective, some may influence freezing, and many are of as yet unknown function. While many of the sequences code for intracellular proteins, a significant number code for apoplastic proteins with a variety of possible functions. Transient influx of calcium into the cytosol appears to be a key step in the response to cold, and also to many other stresses and signals. Similarly, the cold-responsive promoter element identified so far is also responsive to drought and salt. However, how cold is sensed, and any cold-specific aspects of the cold signal transduction pathway, are, so far, unknown. What is clear is that, at least in the model plant Arabidopsis thaliana, cold-, desiccation-, salt- and ABA-triggered signal transduction pathways, and possibly others, run partly in parallel and partly intersect. This may be partly explained by a need for an integrated winter-response. The total number of genes which are cold-responsive and the quantity of resources which this implies are used in this way, indicate that many must have a positive role in acclimation. Experiments which modify membrane lipid unsaturation or solute accumulation, achieved by transformation of plants to express exotic or heterologous genes or by other means, confirm that these factors affect chill- or freezing-tolerance. A transgenic test has shown that one cold-up-regulated gene of previously unknown function contributes to freezing-tolerance, but the small effect re-emphasises the probably cumulative nature of the contributions of many cold-up-regulated sequences to acclimation. On the other hand, mutant analysis indicates some genes may make a comparatively larger contribution. Transformation of alfalfa to overexpress a superoxide dismutase gene increased cold-tolerance and drought-resistance and demonstrated that improvements in field-survival of stresses is possible by transgenic means. Over-expression of a transcription factor, CBF1, conferred freezing-tolerance on Arabidopsis, showing that manipulation of the signal transduction pathway could be an important method for modifying cold-tolerance.
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  • 129
    ISSN: 1573-5168
    Schlagwort(e): fish ; gene expression ; GH ; GtH ; gonad ; growth factors ; RT-PCR ; salmonid
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract In this study, Northern blot analysis of RNA from trout testis revealed a single transcript of insulin-like growth factor II (IGF-II) around 4.7 kb. The cellular distribution of IGF-II mRNA was studied and quantified in different testicular cells enriched populations by RT-PCR. IGF-II mRNA appears to be expressed in all cellular types tested: spermatogonia A and B, primary spermatocytes, spermatids and secondary spermatocytes and Sertoli cells. A significantly higher expression of IGF-II was found in premeiotic germ cells. The levels of IGF-II mRNA appear to be higher than those of IGF-I in immature trout testis, as judged from the semi-quantitative RT-PCR results. These data suggest that in addition to IGF-I, IGF-II may play a role in testicular physiology in fish. The hormonal regulation of IGF-I and IGF-II gene expression was investigated both in vitro and in vivo using RT-PCR approach. Gonadotropin (GtH) added to testicular explants increased IGF-II mRNA levels but had no effect on IGF-I. No statistically significant effect was observed with androgens. In vivo, GH and pituitary extracts resulted in an 8 fold and 2-3 fold increase in both IGF-I and IGF-II mRNA levels, respectively. Taken together, our study suggests that IGF-I and IGF-II may act as local mediators of GH and GtHs in fish testis. Moreover, our results imply that in fish testicular cells, IGFs are potential paracrine/autocrine regulators inside the spermatogenic compartment and can act directly on germ cells to stimulate their proliferation.
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  • 130
    Digitale Medien
    Digitale Medien
    Springer
    Neurochemical research 24 (1999), S. 637-641 
    ISSN: 1573-6903
    Schlagwort(e): Tubulin ; glial fibrillary acidic protein ; gene expression ; human fetal brain
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract Developmental alterations in the expression of glial fibrillary acidic protein (GFAP) and α-tubulin were examined at the level of mRNA and protein in human fetal brain between weeks 13–23 of gestation. Except for a transient increase at week 15, GFAP expression in the cytoskeletal (CSK) fraction was low until week 17, when it increased steadily to week 23, corresponding to the phase of glial proliferation. The developmental profile of α-tubulin in the CSK fraction displayed a biphasic pattern, with an initial rise between weeks 13–16 coinciding with the early phase of neuroblast multiplication, and a second rise between weeks 17–23 corresponding to the phase of glial proliferation. No significant difference in the spatial distribution of α-tubulin was found in different region of brain but GFAP expression varied with a higher level in cerebellum than that in cerebrum at late midgestation.
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  • 131
    Digitale Medien
    Digitale Medien
    Springer
    Journal of bioenergetics and biomembranes 31 (1999), S. 467-473 
    ISSN: 1573-6881
    Schlagwort(e): Uncoupling proteins ; fatty acids ; skeletal muscle ; brown adipose tissue ; obesity ; thermogenesis ; gene expression
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie , Chemie und Pharmazie , Physik
    Notizen: Abstract The recently discovered uncoupling protein 3 (UCP3) is highly homologous to the mitochondrialinner membrane protein UCP1, which generates heat by uncoupling the respiratory chainfrom oxidative phosphorylation. The thermogenic function of UCP1 protects against cold andregulates the energy balance in rodents. We review in vitro studies investigating the uncouplingactivity of UCP3 and in vivo studies, which address UCP3 gene expression in brown adiposetissue and skeletal muscle under various metabolic conditions. The data presented are, for themost, consistent with an uncoupling role for UCP3 in regulatory thermogenesis. We alsodiscuss mediators of UCP3 regulation and propose a potential role for intracellular fatty acidsin the mechanism of UCP3 modulation. Finally, we hypothesize a role for UCP3 in themetabolic adaptation of the mitochondria to the degradation of fatty acids.
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  • 132
    Digitale Medien
    Digitale Medien
    Springer
    Neurochemical research 24 (1999), S. 1233-1240 
    ISSN: 1573-6903
    Schlagwort(e): Anandamide ; AMPA GluR3 receptor subunit ; cannabinoid CB1 receptor ; cAMP ; gene expression ; cannabinoid antagonist ; SR141716A ; Xenopus oocytes
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract The discovery of endocannabinoids such as anandamide and the wide spread localization of cannabinoid receptors in the brain and peripheral tissues, suggests that the cannabinoid system represents a previously unrecognized ubiquitous net work in the nervous system, whose physiology and function is unfolding. In this study, we tested the hypothesis that some of the actions of anandamide are independent of a cannabinoid receptor mechanism. This was accomplished by the use of cannabinoid agonist and antagonist interaction in an in-vitro and in-vivo test systems. In-vitro, we used Xenopus laevis oocytes expression system and two-voltage clamp technique in combination with differential display polymerase chain reaction to determine whether the differential display of genes following treatment with anandamide may be linked to AMPA glutamate receptor. The differential expression of genes in vivo after the sub-acute administration of anandamide could not be directly linked with the AMPA glutamate receptor. In the voltage clamp studies we investigated the effects of anandamide on recombinant AMPA GluR3 sub-unit currents generated by kainic acid in oocytes expressing the AMPA glutamate receptor. In the in-vitro studies, we present evidence that anandamide inhibited the kainate activated currents in oocytes expressing AMPA glutamate receptor involves cAMP transduction via a cannabinoid receptor independent mechanism. In the in-vivo studies, SR141716A, the CB1 antagonist, induced anxiolysis, that was dependent on the mouse strain used in the anxiety model and blocked the anxiogenic effects of anandamide or methanandamide whereas SR141716A had no effect on the anandamide inhibition of kainate activated currents in-vitro.
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  • 133
    ISSN: 1573-6784
    Schlagwort(e): Brevibacillus ; cyclodextrin ; gene expression ; glycosyltransferase ; mannitol ; polyol
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Werkstoffwissenschaften, Fertigungsverfahren, Fertigung
    Notizen: Abstract Expression of Brevibacillus brevis CD162 cyclodextrin glycosyltransferase (CGTase) gene using pET22b(+) vector in Escherichia coli BL21(DE3) resulted in the formation of inactive inclusion bodies under the usual induction conditions. However, by lowering the induction temperature to 30 °C and/or adding 0.5 M mannitol as an osmolyte, the formation of insoluble aggregates was prevented and about a 34-fold increase (8.51 U ml−1) in biologically active soluble form was achieved after 6 h induction. The active CGTase enzyme was estimated to comprise as much as 24% of the total soluble proteins. In addition, other polyols such as glycerol, erythritol, xylitol, sorbitol, and arabitol showed similar effects with mannitol on the production of active CGTase enzyme.
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  • 134
    ISSN: 1573-6903
    Schlagwort(e): Alzheimer's disease ; gene expression ; cytochrome c oxidase: NADH dehydrogenase ; mRNA ; RT PCR
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract In this study, changes of the expression of two mitochondrial and two nuclear genes encoding the subunits of cytochrome c oxidase (CO) and NADH dehydrogenase (ND) were studied in the hippocampus, inferior parietal lobule, and cerebellum of 10 Alzheimer's disease (AD) and 10 age-matched control subjects. The altered proportion between CO II and CO IV mRNAs was observed in the AD brain. Changes of the proportion between CO II and CO IV transcripts may contribute to the kinetic perturbation of CO documented in AD. A coordinated decrease of ND4 and ND15 mRNAs was found in the AD hippocampus and inferior parietal lobule, but not in cerebellum. The decrease of ND4 gene expression may lead to the inhibition of normal ubiquinone oxidoreductase activity of ND. This study suggests that changes of the expression of mitochondrial and nuclear genes, encoding parts of ND and CO enzyme complexes, may contribute to alterations of oxidative metabolism in AD.
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  • 135
    Digitale Medien
    Digitale Medien
    Springer
    Breast cancer research and treatment 54 (1999), S. 269-278 
    ISSN: 1573-7217
    Schlagwort(e): apoptosis ; breast carcinoma ; cell cycle ; curcumin ; cytotoxicity ; gene expression ; RT‐PCR
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract Curcumin has anti‐inflamatory, antiproliferative, and antitumor effects. To understand the chemopreventive mechanism of curcumin against human malignancies, the cellular and molecular changes induced by this agent in human mammary epithelial (MCF‐10A) and breast carcinoma (MCF‐ 7/TH) cell lines were investigated. The human multidrug‐ resistant breast cancer cell line was 3.5 fold more sensitive to curcumin than the mammary epithelial cell line. Even though both cell lines accumulated a similar amount of curcumin, a significantly higher percentage of apoptotic cells was induced in breast cancer cells compared to a very low percentage of apoptosis in mammary epithelial cells. Incubation of breast cancer cells with 20 and 40 μM curcumin for 24 h induced G2 block and sub‐ G0/G1 cell population, respectively. Curcumin treatment caused a reduction in the expression of Ki67, PCNA, and p53 mRNAs in breast cancer cells. The human mammary epithelial cell line showed a down‐regulation of p21 mRNA and an up‐regulation of Bax mRNA expression with curcumin treatment. The results suggest that apoptosis is involved in the curcumin‐induced inhibition of tumor cell growth, and genes associated with cell proliferation and apoptosis may be playing a role in the chemopreventive action of curcumin. Abbreviations: EGF: epidermal growth factor; D-MEM: Dulbecco' Modified Eagle Medium; EDTA: ethylene diamine tetra‐acetic acid; PBS: phosphate buffered saline; TdT: terminal deoxynucleotidyl transferase; FBS: fetal bovine serum; RT‐PCR: reverse transcription‐polymerase chain reaction; PCNA: proliferating cell nuclear antigen; TNF: tumor necrosis factor; TPA: 12‐tetradecanoyl‐phorbol‐13‐acetate.
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  • 136
    ISSN: 1573-7217
    Schlagwort(e): breast cancer ; differential display ; gene expression ; invasion ; metastasis
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract We have previously shown that human breast carcinoma cells demonstrating an interconverted phenotype, where keratin (epithelial marker) and vimentin (mesenchymal marker) intermediate filaments are both expressed, have an increased ability to invade a basement membrane matrix in vitro. This increase in invasive potential has been demonstrated in MDA‐MB‐231 cells, which constitutively express keratins and vimentin, and in MCF‐7 cells transfected with the mouse vimentin gene (MoVi). However, vimentin expression alone is not sufficient to confer the complete metastatic phenotype in MoVi cells, as determined by orthotopic administration. Thus, in the present study, differential display analysis was utilized to identify genes that are associated with the invasive and/or metastatic phenotype of several human breast cancer cell lines. Forty‐four of 84 PCR fragments were differentially expressed as assessed by Northern hybridization analysis of RNA isolated from MCF‐7, MoVi, and MB‐231 cell lines. Polyadenylated RNA from a panel of poorly invasive, invasive/non‐metastatic, and invasive/metastatic breast carcinoma cell lines was used to differentiate between cell‐specific gene expression and genes associated with the invasive and/or metastatic phenotype(s). We observed that lysyl oxidase and a zinc finger transcription factor were expressed only in the invasive and/or metastatic cell line; whereas, a thiol‐specific antioxidant and a heterochromatin protein were down‐regulated in these cells. In contrast, tissue factor was expressed only in breast carcinoma cell lines having the highest invasive potential. These results suggest that specific genes involved in breast cancer invasion and metastasis can be separated by differential display methodology to elucidate the molecular basis of tumor cell progression.
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  • 137
    Digitale Medien
    Digitale Medien
    Springer
    Heart failure reviews 4 (1999), S. 361-378 
    ISSN: 1573-7322
    Schlagwort(e): gene expression ; heart failure ; hypertrophy ; cell signaling ; E-C coupling ; extracellular matrix ; neurohormones ; growth factors ; cytokines ; apoptosis
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract With the advancement in molecular techniques for characterizing genes and the use of animal models as tools to study heart failure, considerable progress has been made in improving our understanding of the regulation and function of genes associated with heart failure. Studies now indicate that autocrine/paracrine factors including neurohormones such as norepinephrine, angiotensin II, proinflammatory cytokines and peptide growth factors produced locally in the heart may affect myocyte growth and function through intricate signaling mechanisms. While changes in gene expression for the proteins involved in cell signaling may lead to myocyte hypertrophy and/or apoptosis, alteration in calcium homeostasis, excitation-contraction coupling and the extracellular matrix also contribute to systolic and diastolic dysfunction leading to heart failure. Thus, heart failure is a complex process, which involves changes in expression of multiple genes. With the advent of new techniques involving microarray and gene chip technology, it is now possible to define and/or identify sets of genes involved in heart failure. The purpose of this review is to provide an overview of molecular signals, intracellular signaling mechanisms and the changes in gene expression associated with the transition from compensated hypertrophy to failure.
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  • 138
    ISSN: 1573-7241
    Schlagwort(e): ventricular remodeling ; myocardial infarction ; diltiazem ; Doppler echocardiography ; gene expression ; cardiac function
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract Summary. The purpose of this study was to examine the effect of diltiazem on cardiac dysfunction and the change in cardiac gene expression after myocardial infarction in rats. On the first day after myocardial infarction, rats were randomly assigned to a diltiazem treatment (Dil, n = 7) or an untreated group (MI, n = 8). We then performed Doppler-echocardiographic examinations on the rats and measured their hemodynamics at 4 weeks after myocardial infarction. Following these measurements, their cardiac mRNA was analyzed. Diltiazem decreased the mean aortic pressure and heart rate. Left ventricular end-diastolic pressure (LVEDP) and central venous pressure (CVP) increased to 18 ± 2 mmHg and 5 ± 1 mmHg (P 〈 0.01). Diltiazem reduced LVEDP to 14 ± 1 mmHg (P 〈 0.05), but it did not change CVP. The weight of the right ventricle in MI was significantly larger than in the control rats (control, n = 7, 0.46 ± 0.02 g/kg vs. MI, 0.81 ± 0.06 g/kg; P 〈 0.01). The left ventricular end-diastolic dimension (LVDd) in MI increased to 8.8 ± 0.3 mm (P 〈 0.01, control, 6.1 ± 0.3 mm). Diltiazem prevented an increase in the weight of the right ventricle (0.69 ± 0.03 g/kg, P 〈 0.05) and LVDd (7.7 ±6 0.2 mm, P 〈 0.05 to MI). The rats within MI showed systolic dysfunction, defined by a decreased ejection fraction (control, 67 ± 2% vs. MI, 36 ± 3%, P 〈 0.01), and diastolic dysfunction, defined by the E-wave deceleration rate (control, 13.4 ± 1.6 m/s2 vs. MI, 30.4 ± 3.4 m/s2 P 〈 0.01). Diltiazem significantly prevented systolic and diastolic dysfunction. The increases in β-MHC, ANP, and collagen type I and III mRNAs in the noninfarcted left ventricle and right ventricle were significantly suppressed by treatment with diltiazem. α-Skeletal actin increased in MI, and α-skeletal actin was more increased with Dil. In conclusion, diltiazem prevents cardiac dysfunction and morphological change due to left ventricular remodeling after experimental myocardial infarction.
    Materialart: Digitale Medien
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  • 139
    ISSN: 1573-7330
    Schlagwort(e): activin ; activin receptors ; semiquantitative RT-PCR ; gene expression ; embryo-endometrium interaction
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract Purpose: Our purpose was to study the role of inhibin/activin during embryogenesis. Methods: Transcripts of inhibin/activin subunits (α, β A , β B ), activin receptors (types I and II), and follistatin were detected by a reverse transcriptase–polymerase chain reaction in human reproductive cells and preembryos cultured alone or co-cultured with human endometrial cells. Results: Transcripts of α, β A , β B subunits were all detected in granulosa luteal cells, but only β A units were detected in endometrial stromal and decidualized cells. In human preimplantation embryos, none of these subunits were detected in embryos from the four-cell to the morula stage and only β A subunits were detectable in blastocyst embryos. Activin receptors were detectable in all of the studied embryos and cells. Transcripts of β A , activin receptors, and follistatin were differentially expressed in human preimplantation embryos cultured in vitro and their expressions were significantly enhanced with the presence of endometrial stromal cells. Conclusions: Our data suggest that there is a possible endometrium–embryo interaction via endometrial activins and preimplantation embryo receptors and that the embryonic expressions of these activins, their receptors, and binding proteins are dependent on embryonic stage.
    Materialart: Digitale Medien
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  • 140
    Digitale Medien
    Digitale Medien
    Springer
    Cancer and metastasis reviews 18 (1999), S. 3-13 
    ISSN: 1573-7233
    Schlagwort(e): minimal residual disease ; metastasis ; gene expression
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract Minimal residual disease (MRD), the tumour burden which remains after a course of treatment that has resulted in clinical remission [1], appears to differ in certain characteristics from the primary tumour population. Certainly the cells which comprise MRD have had to escape from the constraints of the primary tumour mass, invade normal tissue and penetrate small vessels in order to enter the circulation in which they then have had to survive. Such activities are the consequence of the expression of specific proteins and these may well be a reflection of alterations in DNA or RNA levels. Identifying the changes in RNA expression levels between related cell groups exhibiting different phenotypes recently has become a great deal easier as a consequence of developments in analytical procedures such as Differential Display (DD) and Serial Analysis of Gene Expression (SAGE). Application of these procedures to MRD cells recovered from blood, bone marrow or lymph node, should identify novel sequences associated with tumour progression and the development of disseminated disease.
    Materialart: Digitale Medien
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  • 141
    ISSN: 1573-2592
    Schlagwort(e): Chronic fatigue syndrome ; immunology ; exercise ; sedentary ; gene expression
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Medizin
    Notizen: Abstract This study was conducted to evaluate the immunological response to an exhaustive treadmill exercise test in 20 female chronic fatigue syndrome patients compared to 14 matched sedentary controls. Venipuncture was performed at baseline and 4 min, 1 hr, and 24 hr postexercise. White blood cells were labeled for monoclonal antibody combinations and were quantified by FACsan. Cytokines were assayed utilizing quantitative RT/PCR. No group difference was seen in $$\dot VO_{2_{peak} } $$ (28.6 ± 1.6 vs 30.9 ± 1.2 ml · kg−1 · min−1; P 〉 0.05). However, 24 hr after exercise the patients' fatigue levels were significantly increased (P 〈 0.05). The counts of WBC, CD3+CD8+ cells, CD3+CD4+ cells, T cells, B cells, natural killer cells, and IFN-γ changed across time (P's 〈 0.01). No group differences were seen for any of the immune variables at baseline or after exercise (P's 〉 0.05). The immune response of chronic fatigue syndrome patients to exhaustive exercise is not significantly different from that of healthy nonphysically active controls.
    Materialart: Digitale Medien
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  • 142
    ISSN: 1573-5028
    Schlagwort(e): gene expression ; Gossypium hirsutum ; plant defence response ; Verticillium dahliae
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Verticillium wilt is a vascular disease of cotton (Gossypium spp.) caused by the fungal pathogen Verticillium dahliae. To begin to understand the molecular mechanisms of the disease response in cotton cultivars that display superior wilt tolerance, such as Gossypium hirsutum cv. Sicala V-1, a cDNA library was constructed with mRNA isolated from root tissue of Sicala V-1, 24 h after inoculation with V. dahliae. The library was screened by a differential screening technique which was successful in identifying differences in gene expression between uninfected and V. dahliae-infected G. hirsutum root tissue. Among the differentially expressed clones, 51% represented up-regulated genes which had the potential to be involved in the defence response of G. hirsutum. The temporal expression patterns of nine suspected defence response genes were examined by northern blot analysis at several time intervals after inoculation with V. dahliae. The rapid increase in mRNA transcripts corresponding to each of these clones upon infection suggests a role for these genes in the defence response of G. hirsutum. Genes not previously associated with the defence response of the cotton plant, such as those for a 14-3-3-like protein and pathogenesis-related (PR) proteins, have been identified together with presumably novel genes, for which a definite function could not be ascribed.
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  • 143
    Digitale Medien
    Digitale Medien
    Springer
    Plant molecular biology 39 (1999), S. 1063-1071 
    ISSN: 1573-5028
    Schlagwort(e): cell cycle ; gene expression ; in vitro fertilization ; maize ; zygote ; embryogenesis
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Differential screening of cDNA libraries of unfertilized egg cells and in vitro zygotes of maize resulted in the isolation of more than 50 different genes whose expression is up- or down-regulated after in vitro fertilization (IVF). Amoung these genes, we identified a cDNA encoding the eukaryotic translation initiation factor eIF-5A. This highly conserved factor is thought to be necessary for selective mRNA stabilization and translation. It is also the only known protein that contains the unusual amino acid hypusine which is required for biological activity. High transcript amounts are stored in the egg cell, which is, in terms of metabolism, relatively inactive. Upon fertilization transcript amounts decrease, in contrast to metabolically inactive embryos in which the transcript cannot be detected and transcript levels increase upon germination. The expression pattern during the first embryonic cell cycle is also different from that observed during the somatic cell cycle: egg cells in the G0 phase contain high transcript levels, while arrested suspension cells contain few transcripts. In the somatic cell cycle, eif-5A is strongly induced during the G1 phase and transcripts are continuously degraded during the S, G2 and M phases until new induction during the G1 phase of the next cycle. eif-5A, a member of a small gene family in maize, is expressed in most maize tissues investigated. Based on our results, we suggest that the unfertilized egg cell of maize, although relatively inactive regarding its metabolism, is prepared for selective mRNA translation that is quickly triggered after fertilization. We also suggest that the regulation of eif-5A in the first embryonic cell cycle is different from the somatic cell cycle.
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  • 144
    ISSN: 1573-5028
    Schlagwort(e): aquaporin ; canola ; gene expression ; germination ; priming ; salt and osmotic stresses
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Two aquaporin genes were isolated from a cDNA library of canola (Brassica napus L.). The first aquaporin, BnPIP1 of 1094 bp, encoding a putative polypeptide of 287 amino acids with a predicted molecular mass of 30.4 kDa and a pI of 7.8, belongs to the family of plasma membrane intrinsic protein (PIPs) aquaporins. The B. napus aquaporin showed 85–94% identity to the Arabidopsis thaliana PIPs. ABA priming of seed induced high levels of BnPIP1 transcript which remained after subsequent re-drying of the seed. The second aquaporin, Bnγ-TIP2 of 1020 bp, encoded a putative polypeptide of 253 amino acids with a predicted molecular mass of 25.8 kDa and a pI of 5.8. Bnγ-TIP2 showed 83–90% identity to γ-TIP genes from a variety of plant species. Bnγ-TIP2 was expressed only when radicle protrusion occurred in either untreated or primed seeds. Seeds primed with PEG or ABA germinated earlier and showed a higher final percentage of germination than unprimed seed, particularly under salt and osmotic stresses at low temperature. Transcripts of both BnPIP1 and Bnγ-TIP2 genes were present earlier during germination of primed seeds than non-primed seed. From these results, we conclude that BnPIP1 is related to the water transportation required for enzymatic metabolism of storage nutrients at the early stages of canola seed germination whereas Bnγ-TIP2 expression is related to cell growth associated with radicle protrusion. Priming induced the expression of BnPIP1 but had no effect on Bnγ-TIP2.
    Materialart: Digitale Medien
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  • 145
    ISSN: 1573-5028
    Schlagwort(e): Brassica napus ; cauliflower mosaic virus ; epidermis ; gene expression ; light induction ; lipid transfer protein
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract cDNA and genomic clones encoding Brassica napus non-specific lipid transfer proteins (LTP) were isolated and sequenced. The encoded amino acid sequences were very similar to those reported previously for LTPs from B. napus and other species. Sequence information indicates that B. napus contains an LTP gene family. The 5′-flanking region of one gene, designated BnLTP, was fused to GUS and the fusion introduced into Arabidopsis. LTP transcripts and BnLTP-Gus expression were present predominantly in the epidermis of leaf and stem, consistent with the hypothesised function of LTPs in the deposition of cuticular or epicuticular waxes. However, GUS activity was detected in other tissues, including lateral root initials, anthers, stigmas and vascular tissues, which may suggest additional functions. LTP transcript levels in B. napus and Arabidopsis and BnLTP-GUS expression in transgenic Arabidopsis were stimulated by blue and red light but not UV-B. BnLTP promoter activity was also stimulated upon viral infection, at a time when the virus had spread systemically. No increase in expression was observed in response to cold or wounding.
    Materialart: Digitale Medien
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  • 146
    ISSN: 1573-5028
    Schlagwort(e): 1-aminocyclopropane-1-carboxylate synthase ; auxin ; brassinosteroid ; ethylene ; gene expression ; hypocotyl ; promoter ; transgenic tobacco ; Vigna radiata
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Indole-3-acetic acid (IAA) markedly increased ethylene production by inducing the expression of three 1-aminocyclopropane-1-carboxylate (ACC) synthase cDNAs (pVR-ACS1, pVR-ACS6 and pVR-ACS7) in mung bean hypocotyls. Results from nuclear run-on transcription assay and RNA gel blot studies revealed that all three genes were transcriptionally active displaying unique patterns of induction by IAA and various hormones in etiolated hypocotyls. Particularly, 24-epibrassinolide (BR), an active brassinosteroid, specifically enhanced the expression of VR-ACS7 by a distinct temporal induction mechanism compared to that of IAA. In addition, BR synergistically increased the IAA-induced VR-ACS6 and VR-ACS7 transcript levels, while it effectively abolished both the IAA- and kinetin-induced accumulation of VR-ACS1 mRNA. In light-grown plants, VR-ACS1 was induced by IAA in roots, and VR-ACS6 in epicotyls. IAA- and BR-treatments were not able to increase the VR-ACS7 transcript in the light-grown tissues. These results indicate that the expression of ACC synthase multigene family is regulated by complex hormonal and developmental networks in a gene- and tissue-specific manner in mung bean plants. The VR-ACS7 gene was isolated, and chimeric fusion between the 2.4 kb 5′-upstream region and the β-glucuronidase (GUS) reporter gene was constructed and introduced into Nicotiana tabacum. Analysis of transgenic tobacco plants revealed the VR-ACS7 promoter-driven GUS activity at a highly localized region of the hypocotyl-root junction of control seedlings, while a marked induction of GUS activity was detected only in the hypocotyl region of the IAA-treated transgenic seedlings where rapid cell elongation occurs. Although there was a modest synergistic effect of BR on the IAA-induced GUS activity, BR alone failed to increase the GUS activity, suggesting that induction of VR-ACS7 occurs via separate signaling pathways in response to IAA and BR. A scheme of the multiple regulatory pathways for the expression of ACC synthase multigene family by auxin and BR is presented.
    Materialart: Digitale Medien
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  • 147
    Digitale Medien
    Digitale Medien
    Springer
    Plant cell, tissue and organ culture 57 (1999), S. 207-210 
    ISSN: 1573-5044
    Schlagwort(e): biolistics ; gene expression ; haploid ; transformation ; Triticum aestivum
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract Using the PDS-1000/He Biolistic® Particle Delivery System, the microprojectile travel distance, rupture disk pressure and DNA/gold particle concentrations were assessed in order to optimise short and longer-term β-glucuronidase reporter gene expression in microspore-derived embryos of wheat. The effects were also evaluated of using sterile filter paper to support explants and treatment with a high osmoticum medium (0.2 M mannitol/0.2 M sorbitol or 0.4 M maltose). In the optimised procedure, wheat microspore-derived embryos (MDEs), were placed on filter paper and incubated on medium containing 0.4 M maltose, for 4 h pre- and 45 h post-bombardment. Five μl pAHC25 (0.75 mg ml-1 in TE buffer) was precipitated onto 25 μl gold particles (60 mg ml-1 in sterile water), using 20 μl spermidine (0.1 M) and 50 μl CaCl2 (2.5 M). The particles were centrifuged and resuspended in 75 μl absolute ethanol prior to the preparation of 6 macrocarriers. A microprojectile travel distance of 70 mm, a rupture pressure of 1300 p.s.i., and a vacuum of 29′′ Hg were employed. Maltose at 0.4 M in the support medium was the most important factor influencing GUS activity in bombarded tissues. GUS activity, 1 day post-bombardment, reached 52 ± 17 GUS-positive foci/MDE (mean ± s.e.m, n=3), with 17 ± 4 foci/MDE at 15 days, giving a 3.0-fold increase (p〈0.05) compared to expression in MDEs bombarded on medium without a high osmoticum treatment.
    Materialart: Digitale Medien
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  • 148
    Digitale Medien
    Digitale Medien
    Springer
    Biotechnology letters 21 (1999), S. 1-5 
    ISSN: 1573-6776
    Schlagwort(e): bovine growth hormone ; gene expression ; plasmid copy number
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Werkstoffwissenschaften, Fertigungsverfahren, Fertigung
    Notizen: Abstract Effect of copy number on the expression of bovine growth hormone gene (bGH) was investigated using the copy number mutants such as pKBJ10, pBJ(Δ tet)10, pUBJ10-1, and pUBJ10 plasmids. The cells harboring plasmids below 84 copies/cell did not produced detectable levels of bGH. When the ColE1 replicon was replaced with the mutated ColE1 replicon originated from pUC19 plasmid, the copy number was increased to about 300 copies/cell and bGH production was enhanced by 11.5% (pUBJ10-1) and 12.3% of total cell protein (pUBJ10). A large amount of mRNA caused by increment of copy number would be needed to overcome some inhibitory threshold and might be an important factor for regulating bGH expression.
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  • 149
    ISSN: 1573-6822
    Schlagwort(e): cytokines ; gene expression ; in vitro human epidermis ; acute and chronic skin irritation ; predictivity
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie , Medizin
    Notizen: Abstract An in vitro human reconstructed epidermis model (SkinEthic) used for screening acute and chronic skin irritation potential was validated against in vivo data from skin tolerability studies. The irritation potential of sodium lauryl sulfate (SLS), calcipotriol and trans-retinoic acid was investigated. The in vitro epidermis-like model consists of cultures of keratinocytes from human foreskin on a polycarbonate filter. The modulation of cell viability, the release and gene expression of proinflammatory cytokines, interleukins 1α and 8, and morphological changes were evaluated during 3 days as endpoints representative for an inflammatory reaction. The cumulative irritation potential of the topical products was evaluated in a human clinical study by visual scoring and biophysical measurement of inflammatory skin reaction after repeated 24 h applications over 3 weeks under Finn chamber patches. All topical products that were nonirritating in the human study were noncytotoxic and did not induce cytokine expression in the in vitro acute model (day 1 exposure). All irritating controls exhibited specific cell viability and cytokine patterns, which were predictive of the in vivo human data. The ranking of mild to moderate skin irritation potential was based on the lack of cytotoxicity and the presence of cytokine patterns including gene expression specific for each irritant, using the chronic in vitro model (up to 3 days exposure). The human reconstructed epidermis model SkinEthic was shown to be a reliable preclinical tool predicting the irritation potential of topical products. Moreover, it is a useful model in a two-step tiered strategy for screening acute and chronic irritation potential for the selection of vehicles for new topical drugs.
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  • 150
    Digitale Medien
    Digitale Medien
    Springer
    Biotechnology techniques 13 (1999), S. 141-144 
    ISSN: 1573-6784
    Schlagwort(e): promoter probe vector ; gene expression ; transcriptional terminator
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Werkstoffwissenschaften, Fertigungsverfahren, Fertigung
    Notizen: Abstract A new promoter probe plasmid, pMOL618, has been specifically designed to be selective for strong promoter sequences. The plasmid contains two origins of replication which allow it to replicate both in Bacillus subtilis and Escherichia coli, as well as an indicator gene which also functions in both backgrounds. The plasmid is therefore useful in the screening of promoter sequences in both organisms. The stringency of the promoter selection is demonstrated using a known strong promoter.
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  • 151
    Digitale Medien
    Digitale Medien
    Springer
    Cellular and molecular neurobiology 19 (1999), S. 93-108 
    ISSN: 1573-6830
    Schlagwort(e): focal cerebral ischemia ; cerebral infarction ; penumbra ; gene expression ; stress response ; inflammatory reaction
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie
    Notizen: Abstract 1. We review the biochemical and molecular changes in brain with developing cerebral infarction, based on recent findings in experimental focal cerebral ischemia. 2. Occlusion of a cerebral artery produces focal ischemia with a gradual decline of blood flow, differentiating a severely ischemic core where infarct develops rapidly and an area peripheral to the core where the blood flow reduction is moderate (called penumbra). Neuronal injury in the penumbra is essentially reversible but only for several hours. The penumbra area tolerates a longer duration of ischemia than the core and may be salvageable by pharmacological agents such as glutamate antagonists or prompt reperfusion. 3. Upon reperfusion, brain cells alter their genomic properties so that protein synthesis becomes restricted to a small number of proteins such as stress proteins. Induction of the stress response is considered to be a rescue program to help to mitigate neuronal injury and to endow the cells with resistance to subsequent ischemic stress. The challenge now is to determine how the neuroprotection conferred by prior sublethal ischemia is achieved so that rational strategies can be developed to detect and manipulate gene expression in brain cells vulnerable to ischemia. 4. Expansion of infarction may be caused by an apoptotic mechanism. Investigation of apoptosis may also help in designing novel molecular strategies to prevent ischemic cell death. 5. Ischemia/reperfusion injury is accompanied by inflammatory reactions induced by neutrophils and monocytes/macrophages infiltrated and accumulated in ischemic areas. When the role of the inflammatory/immune systems in ischemic brain injury is revealed, new therapeutic targets and agents will emerge to complement and synergize with pharmacological intervention directed against glutamate and Ca2+ neurotoxicity.
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  • 152
    ISSN: 1573-2932
    Schlagwort(e): Ponderosa pine ; elevated CO2 ; growth ; gene expression
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Energietechnik
    Notizen: Abstract Biochemical and gene expression changes in response to elevated atmospheric CO2 were investigated in five maternal half-sibling breeding families of Ponderosa pine. Seedlings were grown in a common garden located at Lawrence Livermore National Laboratory, in open-topped chambers (OTC) for two years. Chamber atmospheres were maintained at ambient, ambient + 175 μL L-1, CO2, or ambient + 350 μL L-1CO2. Growth measurements showed significant increases in stem volumes and volume enhancement ratios in three of the five families studied when grown under elevated CO2. Biochemical and gene expression studies were undertaken to gain a mechanistic understanding of these phenotypic responses. Biochemical studies focused on sucrose phosphate synthase (SPS) specific activities at increase CO2 levels. Kinetic evaluations of SPS showed an increase in VMax. Specific SPS probes revealed increases in the transcriptional levels of one SPS gene with exposure to increasing CO2. RT-PCR differential gene displays showed that overall only a small fraction of visualized gene transcripts responded to elevated CO2 (8-10%). There were also significant differences between the gene expression patterns of the different families, some of which correlated with alterations in growth at elevated CO2 levels.
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  • 153
    Digitale Medien
    Digitale Medien
    Springer
    World journal of microbiology and biotechnology 15 (1999), S. 105-109 
    ISSN: 1573-0972
    Schlagwort(e): Alginate lyase ; gene expression ; polymannuronate lyase ; Pseudomonas sp.
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Biologie , Werkstoffwissenschaften, Fertigungsverfahren, Fertigung
    Notizen: Abstract An alginate lyase named ALYII was purified to homogeneity from Escherichia coli JM109 carrying a recombinant plasmid, pJK26 harbouring the alyII gene from Pseudomonas sp. OS-ALG-9 by column chromatography with DEAE-cellulose, CM-Sephadex C-50, butyl-Toyopearl 650 M and isoelectric focusing. The molecular size of the purified ALYII was estimated to be 79 kDa by SDS-PAGE and its pI was 8.3. The enzyme was most active at pH 7.0 and 30 °C. Its activity was completely inhibited by Hg2+. The enzyme was poly β-D-1, 4-mannuronate-specific rather than β-D-1, 4-guluronate-specific and it showed a promotion effect in alginate degradation by combination with ALY, an another poly β-D-1, 4-mannuronate-specific alginate lyase from the same strain.
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  • 154
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 57-60 
    ISSN: 1434-193X
    Schlagwort(e): Benzyne ; Dehydroanthracene ; Matrix isolation ; Photochemistry ; Bergman reaction ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -9,10-Didehydroanthracene (1) is an interesting derivative of p-benzyne that has been subject of several studies. In contrast to an earlier report, the photochemical decarbonylation of 9,10-dicarbonyl-9,10-dihydroanthracene (2) does not lead to 1 but rather to the ring-opened ene-diyne 4. The key intermediate for this reaction is keto carbene 7 which is formed by monodecarbonylation of 2. Carbene 7 is labile towards visible-light irradiation and easily looses the second CO molecule to give 4. Carbene 7 and diyne 4 are characterized by IR and UV/Vis spectra, the IR spectra are compared to calculations at the B3LYP/6-31G(d,p) level of theory.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
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  • 155
    ISSN: 1434-193X
    Schlagwort(e): Nucleophilic addition ; Solvent effect ; Reversal of diastereoselectivity ; Temperature effect ; Imines ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Commonly observed, but rarely explored, is the possibility of modifying the diastereomeric excess (de%) by means of temperature. A complete reversal in the diastereofacial selectivity could be obtained whenever the diastereoisomers concerned are differentially favored by enthalpy and entropy. The enthalpic or entropic dominance of a diastereoisomer depends greatly on the reaction solvent used.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 156
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 73-81 
    ISSN: 1434-193X
    Schlagwort(e): Donor-acceptor systems ; Cage compounds ; Stelladione ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -A number of condensations could be carried out using tricyclo[3.3.0.03,7]octane-2-one (stellanone, 4) and tricyclo[3.3.0.03,7]octane-2,6-dione (2,6-stelladione, 5) as starting materials. The components for condensations were 2-trimethylsilyl-1,3-dithiane (6), 1,1-bis(trimethylsilyl)-1H-cyclopropa[b]naphthalene (7), its 3,6-dimethoxy-substituted analogue 8, fluorene (12), xanthene (13), diethyl malonate (14), and malononitrile (15). The condensation reactions with 5 yielded mono- and disubstituted products, among them were the donor-acceptor-substituted 2,6-stellanes 33-35. The structures of 18 (prepared from stellanone and fluorene), 19, 24, 27, 31 and 32 (synthesized by condensation of 2,6-stelladione and 2-trimethylsilyl-1,3-dithiane and malononitrile, respectively) were determined by X-ray crystallography.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 157
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 87-90 
    ISSN: 1434-193X
    Schlagwort(e): Water ; α-Nitrocycloalkanones ; ω-Nitro acids ; Surfactant ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The reaction of various α-nitrocycloalkanones 1 with aqueous 0.05 M NaOH, at 80 °C, in the presence of cetyltrimethylammonium chloride (CTACl) as a cationic surfactant, produces ω-nitro acids 2 in good yields. Reduction of the latter with HCOONH4/Pd-C, in methanol, at 80 °C affords ω-amino acids 3. The synthesis of methyl 9-oxodecanoate (8) is also reported.
    Zusätzliches Material: 2 Tab.
    Materialart: Digitale Medien
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  • 158
    ISSN: 1434-193X
    Schlagwort(e): O-Alkylation ; Ambident nucleophile ; Thiazolethione ; Thiohydroxamic acid ; Phase-transfer reaction ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -O-Alkylation of cyclic thiohydroxamic acids 1 and 3-5 has been studied with a view to developing an efficient method for the synthesis of N-(alkoxy)pyridine-2(1H)-thiones and N-(alkoxy)thiazole-2(3H)-thiones. Four issues have been addressed and the following conclusions can be drawn: (i) Thiones 1 and 5 exist as O-H acids in the solid state. (ii) According to NMR investigations (1H, 13C), the thione structures should be largely retained in CDCl3, [D6]DMSO, and CD3OD solutions of acids 1, 3-5, as is also the case for pyridinethione salts 2a-h. (iii) O-Alkylation of pyridinethione salts occurs in competition with S-alkylation. Selective O-alkylation is however possible, if thiohydroxamate salts with large countercations, such as M = NBu4, are treated with hard alkylating reagents in polar aprotic media. (iv) As tetrabutylammonium thiohydroxamates, such as 2f, are highly useful in the synthesis of cyclic thiohydroxamic acid O-esters, we have developed an efficient protocol for the preparation of N-(alkoxy)pyridine-2(1H)-thiones directly from acid 1 using phase-transfer conditions (alkyl halide or sulfonic acid ester, CH3CN, K2CO3, Bu4NHSO4). This method has proved particularly successful for the synthesis of N-(alkoxy)thiazole-2(3H)-thiones 11, 20-28, which were obtained in yields of up to 87%.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
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  • 159
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 129-134 
    ISSN: 1434-193X
    Schlagwort(e): Tetrahydro-2-vinylquinoxaline ; Cyclization ; Palladium ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Reaction of (Z)-1,2-bis(methoxycarbonyloxy)but-2-ene (2) with various N,N-bis(arylsulfonyl)-o-phenylenediamines 1 was catalyzed by a palladium complex associated with chiral ligands to give optically active 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydro-2-vinylquinoxalines 3 with up to 62% ee. The use of (S)-MeOBIPHEP as the chiral ligand and N,N-bis(p-tolylsulfonyl)-o-phenylenediamine (1i) as the nucleophile led to the highest ee at 25 °C, regardless of the solvent used. The enantioselectivity of the cyclization is strongly affected by the nature of the substituents at the nitrogen atom.
    Zusätzliches Material: 4 Tab.
    Materialart: Digitale Medien
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  • 160
    ISSN: 1434-193X
    Schlagwort(e): Fluorine ; Lactones ; Annulation ; Ketene ; Sulfoxides ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Enantiomerically pure α,α-dichloro β-fluoroalkyl γ-p-tolylthio γ-butyrolactones trans-6a-c have been obtained with excellent stereocontrol (〉 98:2) and enantiomeric purity (〉 98:2) by sulfoxide-directed lactonization (Marino's annu-lation reaction) of β-fluoroalkyl vinyl sulfoxides (R)-(E)-5a-c with dichloroketene. Highly chemoselective dechlorination and desulfurization reactions performed on trans-6c efficiently provided the β-chlorodifluoromethyl γ-butyrolactone (S)-8c, the absolute stereochemistry of which was determined by X-ray diffraction analysis of its γ-p-tolylthio precursor (2R,3S)-7c.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 161
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 141-143 
    ISSN: 1434-193X
    Schlagwort(e): Nitrosobenzene ; 4-Methoxy-N-methyleneaniline ; 1,3,5-Tris(4-methoxyphenyl)-1,3,5-triazinane ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -A 1:1 adduct produced in the reaction of nitrosobenzene (2) with 1,3,5-tris(4-methoxyphenyl)-1,3,5-triazinane (3) has been shown by X-ray diffraction structure analysis to be the N′-(4-methoxyphenyl)-N-phenyl-N-oxyformamidinium species 5.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 162
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 155-161 
    ISSN: 1434-193X
    Schlagwort(e): Alkylation ; Oxazolines ; anti-α-Alkyl α-hydroxy β-amino acids ; Lithium dianion ; Penicillin G acylase ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -As part of an ongoing project concerning the synthesis of enantiomerically pure α-hydroxy β-amino acids, we have now developed a general strategy allowing the synthesis of anti-α-alkyl α-hydroxy β-amino acids. Our procedure involves the intermediate formation of trans-oxazolines, which are alkylated at C-5 with good to high diastereoselectivity and then hydrolysed under mildly acidic conditions, affording in quantitative yield the corresponding hydroxy amides. The starting (R)-3-amino-3-phenylpropanoic acid and (S)-3-aminobutanoic acid were obtained in enantiomerically pure form by selective enzymatic hydrolysis of the corresponding phenylacetylamides with penicillin G acylase.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
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  • 163
    ISSN: 1434-193X
    Schlagwort(e): Palladium catalysis ; Homogeneous catalysis ; Anilines ; Alkylation ; Oxazolidinones ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Palladium-catalyzed reaction of acidic anilines with (Z)-2-butene-1,4-diyl dicarbonate affords N-aryl-4-vinyloxazolidin-2-ones. The success of the reaction depends on the acidity of the aniline and requires in situ conversion of the dicarbonate into carbamate carbonate by nucleophilic attack of the aniline conjugate base followed by palladium-catalyzed intramolecular cyclization.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 164
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 215-220 
    ISSN: 1434-193X
    Schlagwort(e): Density functional calculations ; Vinylcyclopropane-cyclopentene rearrangement ; [1,3]-Sigmatropic shift ; Biradical-like transition structure ; Substituent effects ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The effect of donor substitution by the hydroxy group and of acceptor substitution by the cyano group on the activation energies of the vinylcyclopropane-cyclopentene rearrangement was calculated by the spin-restricted RB3LYP/6-31G* method for reactant structures and by the spin-unrestricted UB3LYP/6-31G* method for transition structures. The activation energies of the rearrangement of hydroxy- and cyano-substituted vinylcyclopropanes are very similar for substitution in the same position. In agreement with earlier findings the substituent effects on the activation energies are closely connected with the radical stabilizing properties of the substituents. As indicated by singlet/triplet splitting energies, the transition structures are essentially biradicaloid. In spite of spin pairing in the transition structure the substituent effects on bond lengths and on stabilization energies are very similar to those of the free radicals corresponding to the two radical substructures. Thus, the transition structures may be considered, in good approximation, as structures consisting of two weakly interacting radicals.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98349_s.pdf or from the author.
    Zusätzliches Material: 5 Ill.
    Materialart: Digitale Medien
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  • 165
    ISSN: 1434-193X
    Schlagwort(e): Cyclopropanes ; Rearrangements ; Cyanohydrins ; Schiff bases ; Small ring systems ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The direct cyclization of 2-amino-4-chloro-3,3-dimethylbutanenitrile with potassium tert-butoxide in THF afforded 1-amino-2,2-dimethylcyclopropane-1-carbonitrile and a dimerization product. Various new cis- and trans-1-(tert-butylamino)-2-benzyl-2-methylcyclopropane-carbonitriles and© the corresponding cyclopropanecarboxamides have been synthesized, with focus on the isolation of the pure stereoisomeric cyclopropanecarboxamides. The relative configuration of the stereoisomers was established by X-ray crystallographic analysis of one of the model compounds. A new route to the latter functionalized cyclopropanes was developed by reaction of 1-methoxycyclopropylamines with potassium cyanide. Some remarkable rearrangements of 1-aminocyclopropane-1-carbonitriles into azetidine and oxazine derivatives via Favorskii-derived intermediates are reported. Various aspects of the chemistry of geminally functionalized cyclopropanes are discussed.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 166
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 267-275 
    ISSN: 1434-193X
    Schlagwort(e): Vinylallenes ; Organocuprates ; Substitution ; Stereoselective synthesis ; Copper catalysis ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Enyne acetates 2, 4, 6, and 8, as well as enyne oxiranes 10, with different substitution patterns react with organocuprates regioselectively under 1,5-(SN2′′)-substitution to provide vinylallenes 11 and 12. With lithium dimethylcuprate, reduced vinylallenes originating from a (formal) transfer of a hydride ion to the substrate are formed in some cases. The products are usually obtained as mixtures of (E/Z)isomers; however, pure (E)-vinylallenes are formed occasionally. The 1,5-substitutions can also be carried out with catalytic amounts of copper reagents. The reaction of chiral enyne acetate (S)-2a with tBu2CuLi · LiCN proceeds enantioselectively, so that this transformation constitutes a new case of remote stereocontrol.
    Zusätzliches Material: 1 Tab.
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  • 167
    ISSN: 1434-193X
    Schlagwort(e): Nitrogen heterocycles ; Open-chain analogue of Reissert compound ; Hydrofluoroborate salts ; α,β-Ethylenic esters ; 1,3-Dipolar cycloaddition ; Azomethine ylide ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The reaction of the hydrofluoroborate salt of an open-chain analogue of a Reissert compound with some α,β-ethylenic esters does not give a [4 + 2] cycloadduct, as previously described in the case of ethyl acrylate. The reaction starts with a 1,3-dipolar cycloaddition of a münchnone imine 5c, d. The [3 + 2] cycloadducts 13 evolve via a rearrangement-condensation sequence to give a substituted 2-pyridone derivative 18 or 19. The proposed mechanism has been verified by the isolation and structural X-ray analysis of some compounds of the reaction sequence.
    Zusätzliches Material: 5 Ill.
    Materialart: Digitale Medien
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  • 168
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 335-360 
    ISSN: 1434-193X
    Schlagwort(e): 2-tert-Butylhydropyrimidinones ; 3-Aminocarboxylic acid derivatives ; Cyclic imino esters ; Lithium enaminates ; Alkylations ; β-Amino acids ; Asymmetric synthesis ; Kinetic resolution ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Racemic and enantiopure 2-tert-butyltetrahydropyrimidinones (from pivalaldehyde and 3-aminocarboxylic acids) are converted to Alloc-, Boc-, and Z-protected cyclic imino esters (7-10, Schemes 2-4). These are deprotonated to Li enaminates (K, L). Reactions with electrophiles (prim., sec. alkyl, allyl, benzyl, propargyl halides, aldehydes, imines, enoates) give good yields and are highly diastereoselective (products 11-42, Schemes 5-10). A two-step cleavage (removal of protecting group and hydrolysis) under very mild conditions converts the heterocyclic products to α-branched β-amino acid methyl esters (43-61, Schemes 11-13). The structure of the products is determined by NMR spectroscopy (Figure 1), by chemical correlation (Scheme 14), and by X-ray analysis (Figure 2, 3, 7, Table 1). A structure of the Li enaminates is proposed (Figure 4). Mechanistic models are derived for the reactions occurring with formation of two stereogenic centers with relative topicity like (Figures 5, 6).
    Zusätzliches Material: 7 Ill.
    Materialart: Digitale Medien
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  • 169
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 373-378 
    ISSN: 1434-193X
    Schlagwort(e): Alkaloids ; Cross-coupling ; N-Heterocycles ; Palladium ; Synthesis design ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Thermal or acetyl chloride induced cyclization of bromoenamide 10 affords the pentacyclic derivative 12 with high yield and regioselectivity. From this common synthetic intermediate, palladium-catalyzed reactions allow the total synthesis of indolopyridine alkaloids 1-6.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98332_s.pdf or from the author.
    Materialart: Digitale Medien
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  • 170
    ISSN: 1434-193X
    Schlagwort(e): Reverse-turn mimics ; γ-Turns ; β-Turns ; β-Hairpins ; NMR spectroscopy ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The solid-phase synthesis and characterization of a series of peptides (3-9), containing reverse-turn mimetic bicyclic lactams (1a, 1b), was reported in the preceding paper. The bicyclic lactams (1a, 1b) possess high structural similarity to the two central residues of a β-turn. The conformational preferences of the constrained peptides have been investigated by NMR spectroscopy and IR spectroscopy. Our experimental results have been complemented by computer modelling studies and show that the constrained peptides (3-9) form an inverse γ-turn or a type-II′ β-turn through intramolecular hydrogen bonding, depending on the nature of the reverse-turn mimic. In N-acetylated tetrapeptide mimics incorporating the two different bicyclic lactams (a series and b series), H5 is available for either a γ-turn (7-membered ring with the carbonyl group of the bicyclic lactam) or a β-turn (10-membered ring with the carbonyl group of residue 2), as shown in Figures 7 and 9. The a series incorporating the (5,7)-bicyclic lactam predominantly induces the γ-turn conformation, while the b series incorporating the (5,6)-bicyclic lactam can promote either a γ-turn or a β-turn conformation, with the β-turn usually being preferred and with varying degrees of β-hairpin formation.
    Zusätzliches Material: 10 Ill.
    Materialart: Digitale Medien
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  • 171
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 409-417 
    ISSN: 1434-193X
    Schlagwort(e): Deprotonation ; Oxiranyloxazolines ; Oxazolinyloxiranyllithium compounds ; Oxazolidines ; Acyloxiranes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at -100 °C in Et2O furnishes oxazolinyloxiranyllithium compounds[1]1b, 1i, and 1l which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c-1g and 1j. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-(4,4-dimethyl-2-oxazolinyl)-2-p-tolylepoxyethane (1h) was found to be configurationally stable while oxiranyllithium 1l, generated from the cis isomer 1k, was not. Oxazolinylepoxides 1d, 1j, and 1m could be deblocked to acyloxiranes 5a-e through oxazolidines 4a-e.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
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  • 172
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 419-430 
    ISSN: 1434-193X
    Schlagwort(e): Electrochemistry ; Electrosynthesis ; Nitrosobenzenes ; Nitrogen heterocycles ; 1-Aminoindoles ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -An electrochemical methodology offering efficient access to N-alkyl- and N-aryl-substituted 1-aminoindoles has been developed. N-Substituted 2-(ortho-nitrosophenyl)ethylamines, electrogenerated in a “redox” flow cell, undergo intramolecular cyclization to hydrocinnoline-type intermediates. Under slightly basic conditions, these undergo spontaneous ring-contraction to produce the N-substituted heterocycles in good yields. The reactions have been studied in slightly acidic and slightly basic aqueous alcoholic media.
    Zusätzliches Material: 11 Ill.
    Materialart: Digitale Medien
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  • 173
    ISSN: 1434-193X
    Schlagwort(e): Aminoacylsilanes ; Amino aldehydes ; Amino alcohols ; Allylation ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -A practical route is described for the synthesis of enantiopure β- and γ-amino alcohols with two stereocenters, starting from homochiral α- (1 and 5) and β- (13 and 16) -aminoacylsilanes, and involving stereoselective addition of allylmetal compounds and subsequent stereospecific protiodesilylation of the adducts. The degree of diastereoselectivity achieved in the nucleophilic addition step depends on both the nitrogen-protecting group and the reagents used. Diastereomeric excess (de) values equal to or higher than 98% were obtained in the TiCl4-promoted allylation of the N-Pht-aminoacylsilanes 1 and 13 and of the N-Ts-aminoacylsilane 5 with allyltrimethylsilane. Lower de values were obtained in the Sc(OTf)3-catalyzed allylation of 5 with tetraallyltin and in the additions of both allyltrimethylsilane and tetraallyltin to the N-Ts-β-aminoacylsilane 16. Protiodesilylation of the adducts, leading to the β- and γ-amino alcohols, was accomplished with TBAF, except in the case of the adducts obtained from 5. For these, a preliminary removal of the tosyl group was necessary, which was accomplished with simultaneous desilylation by treatment with Na in liquid ammonia.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98342_s.pdf or from the author.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 174
    ISSN: 1434-193X
    Schlagwort(e): meta Photocycloaddition ; Photochemistry ; Steric hindrance ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Irradiation of a series of 5-(2-methoxyphenyl)pent-1-enes substituted with a hydroxy or trimethylsilyloxy group at the α-, β-, or γ-position of the side-chain yields in all cases meta photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that the diastereoselectivity originates from minimization of steric interactions between the side-chain substituent and the ortho-methoxy group at the arene unit. Hydrogen bonding does not seem to be involved. The introduction of the side-chain substituents also influences the regioselectivity of the addition: The linear to angular adduct ratios are significantly increased compared to the case of the parent compound.
    Zusätzliches Material: 3 Tab.
    Materialart: Digitale Medien
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  • 175
    ISSN: 1434-193X
    Schlagwort(e): 5-Aza-7-deaza-2′-deoxyguanosine ; Oligonucleotides ; Parallel DNA ; Protonated base pairs ; Tm values ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Oligonucleotides containing 5-aza-7-deaza-2′-deoxyguanosine (1) were synthesized. Solid-phase synthesis was performed with the phosphonate 15 or the phosphoramidite 5. The amino-unprotected phosphonate 4 was also employed. Hybridization studies of oligonucleotides containing 1 resulted in new base pairs leading to duplexes with parallel (ps) or antiparallel (aps) chain orientation. Among those with parallel chains a stable “purine-purine” base pair was observed between 5-aza-7-deazaguanine and guanine or 7-deazaguanine. Antiparallel stranded duplexes are formed when 5-aza-7-deazaguanine pairs with cytosine. This base pair has only two hydrogen bonds under neutral conditions but is stabilized by a third one in acidic medium. A new base pair is also detected between the base of 1 and isoguanine (neutral medium).
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 176
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 523-523 
    ISSN: 1434-193X
    Schlagwort(e): Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -By mistake wrong concentrations were given in the footnote of Table 1 and in the Discussion. Instead of c0 = 1.2 M read c0 = 0.12 M if 2-naphthalenethiol was used as hydrogen donor and instead of c0 = 1.8 M read c0 = 0.18 M if Bu3SnH was used to trap photoproducts. In Table 2 relative rate constants of radical 2d refer to radical 2e and vice versa as correctly stated in the Discussion. In the Experimental Section (Iodocyclization) read 2.25 g (8.86 mmol) of iodine instead of 2.25 g (1.10 mmol) of iodine.
    Materialart: Digitale Medien
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  • 177
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 527-538 
    ISSN: 1434-193X
    Schlagwort(e): Tris(pentafluorophenyl)borane ; Diarylborinic acid ; Arylboronic acid ; Chiral arylboron catalyst ; Lewis acid ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Arylboron compounds, ArnB(OH)3-n (n = 1-3), bearing electron-withdrawing aromatic groups such as triarylboranes, diarylborinic acids, and arylboronic acids represent a new class of air-stable and water-tolerant Lewis acid or Brønsted acid catalysts in organic synthesis. In particular, while tris(pentafluorophenyl)borane has primarily been used as a co-catalyst in metallocene-mediated olefin polymerization, its potential as a Lewis acid catalyst for organic transformation is now much more extensive. Diarylborinic acids and arylboronic acids have shown themselves to be powerful tools in the design of chiral boron catalysts. This article provides a comprehensive summary of the organic transformations catalyzed by arylboron compounds as acids.
    Zusätzliches Material: 2 Ill.
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  • 178
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 573-577 
    ISSN: 1434-193X
    Schlagwort(e): Structure elucidation ; Constitutional analysis ; Natural products ; HMBC ; Computational chemistry ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The computer program COCON is introduced as a tool for the comprehensive structure elucidation of unknown organic compounds. In particular, structural proposals made on the basis of the molecular formula and of 2D-NMR experiments can be analyzed for the existence of alternative constitutions being in agreement with the same data set. The computational speed grounds on the evaluation of ambiguous long-range connectivity information during the process of structure generation. The data set experimentally obtained for the marine natural product oroidin (1) was selected, because proton-poor compounds usually cause uncertainties in NMR-based structure determinations. The calculation results encourage to move from the experience-based analysis of NMR chemical shifts or of MS fragmentations to the automated evaluation of routinely available connectivity information.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98241_s.pdf or from the author.
    Zusätzliches Material: 6 Ill.
    Materialart: Digitale Medien
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  • 179
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 587-595 
    ISSN: 1434-193X
    Schlagwort(e): Phosphaalkenes ; Heterodiphospholes ; Cycloadditions ; Phosphaalkyne cyclooligomers ; Phosphorus-carbon cage compounds ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The first synthesis of a 1,2,4-oxadiphosphole 6 has been achieved by vacuum thermolysis of mesitylphosphaalkene 5. The novel heterocycle 6 exhibits an enormous potential for cycloaddition reactions, which predominantly proceed selectively at low temperatures. Compound 6 undergoes addition with two equivalents of phosphaalkynes 10 by a [4+2] cycloaddition/homo Diels-Alder reaction sequence to form novel oxatetraphosphadeltacyclenes 12 and 13. Tetrachloro-o-benzoquinone (14) undergoes a selective [4+1] cycloaddition with 12 and 13 leading to the spirocyclic products 15 and 16 containing λ5-phosphorus atoms. Treatment of the oxadiphosphole 6 with dimethyl acetylenedicarboxylate (17) provides the first access to a 1,2-oxaphosphole 18, which is formed after an initial [4+2] cycloaddition followed by a retro Diels-Alder reaction. An unexpected reaction of 6 is observed with tri-tert-butylazete (20) furnishing a new polycyclic system (→ 21).
    Zusätzliches Material: 4 Ill.
    Materialart: Digitale Medien
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  • 180
    ISSN: 1434-193X
    Schlagwort(e): 1β-Methylcarbapenems ; Palladium ; Ruthenium ; Catalysis ; Cyclizations ; Stereoselective hydrogenation ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -An efficient diastereoselective multi-step synthesis of bicyclic 1β-methylcarbapenem antibiotic precursors has been developed, starting from the commercially available 4-acetoxyazetidin-2-one 4. Chiral ruthenium catalysts are used in the hydrogenation step to control the β-stereochemistry at the 1-position, and a π-allylpalladium ring-closure strategy is used to form the functionalized carbapenem skeleton.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 181
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 643-651 
    ISSN: 1434-193X
    Schlagwort(e): Oligomers ; Synthesis design ; Substituent effects ; Luminescence ; Cyclic voltammetry ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Synthetic strategies towards appropriate symmetric and unsymmetric functionalization of the naphthalene ring are presented. By means of Knoevenagel and Wittig condensation reactions new fluorescent, differently functionalized oligo(2,6-naphthylenevinylene)s have been synthesized, the presence of terminal aldehyde or bromine substitution opening the way to the incorporation of the fluorescent trimers in a variety of polymeric materials. The effect of substituting the phenylene ring by the more bulky dialkoxynaphthalene system in arylenevinylene-type materials is studied from the structural point of view and the possibility to tune the emission color and the electron affinity through the introduction of naphthylenevinylene and cyano-substituted naphthylenevinylene units is also investigated.
    Zusätzliches Material: 4 Ill.
    Materialart: Digitale Medien
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  • 182
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 661-664 
    ISSN: 1434-193X
    Schlagwort(e): Aziridines ; N-Heterocycles ; Fatty acids ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The first successful preparation of the aziridines methyl cis-9,10;cis-12,13-diepiminooctadecanoate (3) derived from linoleic acid, and methyl cis-9,10;cis-12,13;cis-15,16-triepiminooctadecanoate (6) derived from linolenic acid, is reported. Remarkably, the bis- and trisaziridine were obtained in a reaction sequence that consists of only two steps, using technically pure methyl esters of epoxidized sunflower and linseed oil. The conversion of methyl 9,10;12,13-diepoxyoctadecanoate (1), with sodium azide and ammonium chloride in ethanol in the presence of water, yielded the new diazidodihydroxy compound methyl 9(10),12(13)-diazido-10(9),13(12)-dihydroxyoctadecanoate (2) in the first step. 2 was obtained as a regioisomeric mixture. The reaction of 2 with triphenylphosphane led to the bisaziridine 3. The analogous conversion of methyl 9,10;12,13;15,16-triepoxyoctadecanoate (4), via the new triazidotrihydroxy compound methyl 9(10),12(13),15(16)-triazido-10(9),13(12),16(15)-trihydroxyoctadecanoate (5), afforded trisaziridine 6.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 183
    ISSN: 1434-193X
    Schlagwort(e): Cavitands ; Nuclear waste ; Actinide/lanthanide separation ; Solvent extraction ; Sulfur atoms ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Cavitands with phosphane sulfide moieties 4 and 8a,b were prepared in good yields from their phosphane oxide analogues, as more stable alternatives for the dithiophosphinic acids used at present. The cavitands 7a and 7b with flexible butoxyphosphane oxide ligating sites are more efficient than cavitand 3 having rigid methylphosphane oxide groups as was studied with EuIII picrate extractions. Due to the absence of an ionic functionality in the phosphane sulfides 4 and 8a,b AmIII and EuIII are not extracted, not even in the presence of synergents (e.g. TBP, TOPO, HDNNS). Cavitand 10 with phosphinic acid groups efficiently extracts EuIII in 1:1 or 2:1 complexes, depending on the metal-to-ligand concentration ratio (extraction constants Kex1 = 3.9·10-5M2 and Kex2 = 1.9·102M, respectively). Furthermore, in the case of 10 EuIII is preferentially extracted over AmIII with a separation factor SEu/Am up to 5.
    Zusätzliches Material: 5 Ill.
    Materialart: Digitale Medien
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  • 184
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 691-696 
    ISSN: 1434-193X
    Schlagwort(e): Carbohydrates ; 4-Thiofuranosides ; Nucleosides ; Reaction mechanisms ; NOE measurements ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabino-furanose (9) has been prepared from D-xylose via the 1,4-dithio-L-arabino-furanoside 8. The crucial step of the reaction, i.e. the intramolecular cyclization of the open-chain dithioacetal 5, has been achieved in a yield of 90% by applying tetrabutylammonium iodide as promoter. Reaction of 9 with bis(trimethylsilyl)uracil or -thymine led to the benzyl derivatives 12 and 13 from which the deprotected 4′-thionucleoside analogues 14 and 15 have been prepared by debenzylation with boron tribromide.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 185
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 737-750 
    ISSN: 1434-193X
    Schlagwort(e): Baeyer-Villiger oxidation ; Ketones ; Monopersulfate ; Peracids ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -In the present review, we report the discovery of the formation of esters and lactones by oxidation of ketones with a peroxide derivative, namely the Baeyer-Villiger reaction. This reaction was first reported by Adolf von Baeyer and Victor Villiger a century ago in 1899, just one year after the oxidant they used (KHSO5) has been described. Furthermore, Baeyer and Villiger established the composition of this new inorganic peroxide and showed that its instability was the reason of a controversy between several European chemists between 1878 and 1893. For the first 50 years the mechanism of the Baeyer-Villiger reaction was a matter of debate. A side product, 1,2,4,5-tetraoxocyclohexane, was ruled out as an intermediate in the ester formation by Dilthey. Criegee postulated a nucleophilic attack of the oxidant on the carbonyl group. This mechanism was confirmed by von E. Doering by a labeling experiment with [18O]benzophenone. The rearrangement step occurs with retention of the stereochemistry at the migrating center. The competitive migration and the rate-determining step are also discussed in this review.
    Zusätzliches Material: 4 Ill.
    Materialart: Digitale Medien
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  • 186
    ISSN: 1434-193X
    Schlagwort(e): Transglycosylation ; Glycosidases ; Thermus thermophilus ; Carbohydrates ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The aim of this paper is to test the ability of a β-glycosidase from Thermus thermophilus to catalyse transglycosylation reactions in the presence of nitrophenyl glycosides as donors and other monosaccharides as acceptors. Our results show that this enzyme is able to induce such reactions either with nitrophenylgalactosides, -glucosides and -fucosides. With the two former donors, the autocondensation of the donor, which thus acts also as an acceptor, is faster than the transglycosylation with other acceptors. Furthermore, as the regioselectivity of the reactions is mainly of the β-[1→3] type, good yields are obtained for the synthesis of 2-nitrophenyl-β-D-galactopyranosyl-[1→3]-β-D-galactopyranoside and 2-nitrophenyl-β-D-glucopyranosyl-[1→3]-β-D-glucopyranoside. Conversely, in the presence of p-nitrophenylfucoside, the autocondensation is very limited, and with methyl-α-D-galactoside as an acceptor, the regioselectivity is mainly of the β-[1→6]-type resulting in the synthesis of methyl-β-D-fucopyranosyl-[1→6]-α-D-galactopyranoside.
    Zusätzliches Material: 7 Ill.
    Materialart: Digitale Medien
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  • 187
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 775-779 
    ISSN: 1434-193X
    Schlagwort(e): Monoynes ; Polyynes ; Alkali metals ; Liquid NH3 ; Hexamethylphosphoric triamide ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Efficient procedures have been developed for the stereospecific reduction by alkali metals of disubstituted acetylenes with long carbon chains. Acetylenes containing two or more (isolated) triple bonds are reduced considerably more easily than are monoynes.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 188
    ISSN: 1434-193X
    Schlagwort(e): Aminophenols /Asymmetric synthesis ; C-C coupling ; Reductions ; Conformation analysis ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Enantiopure o-hydroxybenzylamines 2a-i were synthesized by diastereoselective reduction of the 2-imidoylphenols (R)-1a-i. Conformational analysis enabled the assignment of the absolute configurations of compounds 2a-i. The accessible o-hydroxybenzylamine (R,R)-2h serves as an effective catalyst precursor for highly enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes. This pathway represents a practical and operationally very simple methodology for the enantioselective synthesis of both the enantiomers of secondary alcohols 7a-f.
    Zusätzliches Material: 4 Ill.
    Materialart: Digitale Medien
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  • 189
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 837-846 
    ISSN: 1434-193X
    Schlagwort(e): Friedel-Crafts reaction ; Hydroxyalkylation ; Aromatics ; Epoxides ; Zeolites ; Clays ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Solid acids, such as zeolites and clays, catalyse the intramolecular hydroxyalkylation (cyclialkylation) of several arylalkyl epoxides in moderate to excellent conversions and selectivities. The use of solid acids in these cyclialkylations provides a cleaner, better alternative to conventional Lewis and Brønsted acids, enabling a more facile workup of reaction mixtures and, in several cases, better selectivities.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
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  • 190
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 861-868 
    ISSN: 1434-193X
    Schlagwort(e): Red phosphorus ; Phosphane PH3 ; Phosphorylations ; Ultrasound irradiation ; Redox chemistry ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The reactivity of red phosphorus towards aldehydes was investigated under basic and acidic media. It was demonstrated that the real phosphorylating agent involved in the reaction was phosphane (PH3) in basic media, and hypophosphorous acid (H3PO2) in acidic media. A convenient one-pot synthesis of (α-hydroxyalkyl)phosphinic acids from red phosphorus and aldehydes in basic media was realized under sonication. The same reaction under acidic media in the presence of hydriodic acid led to the corresponding phosphonic acids. The (α-hydroxyalkyl)phosphinic acids were readily prepared under sonication from hypophosphorous acid and aldehydes in the presence of catalytic amounts of hydrochloric acid. The mechanism of the addition reaction of PH3 to benzaldehyde was elucidated and shows the complexity of the reaction as a function of the experimental conditions.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 191
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 909-915 
    ISSN: 1434-193X
    Schlagwort(e): Erythrina alkaloids ; Nitrogen heterocycles ; Nitro aldol reaction ; Michael addition ; Pummerer reaction ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -A successful new strategy for the synthesis of erythrinanes is reported. (Nitromethyl)arene derivative 16 was condensed with aldehyde 17 to give nitro aldol 19. After removal of the hydroxy group, the subunits 26a,b, containing the erythrinane rings A and D, were formed by intramolecular Michael addition. Reduction of the nitro function, followed by cyclization of the resulting amino group with the appended acetate group afforded the bicyclic lactams 29a,b, bearing an angular aryl group. Two-carbon elongation at the nitrogen atoms of 29a and 29b by means of hetero Michael addition of methyl phenyl sulfoxide, followed by Pummerer-type cyclization, gave cis- and trans-11-phenylthioerythrinan-8-ones 35a and 35b, respectively. Reductive desulfurization at C-11 furnished the desired erythrinan-8-ones 39a and 39b in 8 steps from 16.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 192
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 917-922 
    ISSN: 1434-193X
    Schlagwort(e): Crystal engineering ; Diynes ; Photochemistry ; Solid-state chemistry ; Polymers ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diynes 4a-c were obtained from the corresponding 2,5-dimethoxybenzenes 1 by bromination followed by a copper-catalyzed Grignard reaction with 3-bromoprop-1-yne. Catalyzed coupling of the resulting 3-(2,5-dimethoxyphenyl)prop-1-ynes 3 under Hay conditions gave the hexa-2,4-diynes 4a-c in good yields. The molecular structures of the diynes 4a and 4b were determined by X-ray diffraction analysis. In each crystal structure, an unusual 1,6-synperiplanar conformation of the hexa-2,4-diyne unit is observed, with the 1,6-diphenyl substituents arranged in a coplanar orientation. According to the crystal structure data obtained, irradiation of diynes 4a and 4b afforded the deeply-colored, highly-ordered polymers 5a and 5b under topochemical control. Oxidation of 4a and 4b with cerium(IV) ammonium nitrate gave the corresponding 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diyne-1,6-diones 6a and 6b.
    Zusätzliches Material: 5 Ill.
    Materialart: Digitale Medien
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  • 193
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 931-936 
    ISSN: 1434-193X
    Schlagwort(e): Nucleosides ; Phosphonates ; Nucleophilic additions ; C-C coupling ; Reduction ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Acyclic carba-nucleoside phosphonates, modelled on natural deoxyribonucleotides have been prepared starting from DNA nucleobases and tert-butyl acrylate. The products obtained from a Michael-type reaction were elongated to β-oxo esters that were first reduced to β-hydroxy esters and then transformed into protected β-hydroxy aldehydes. Wittig-Horner-Emmons reaction with the anion of tetraisopropyl methylenebisphosphonate gave, after deprotection, the desired 4-hydroxy-6-purinyl- or -6-pyrimidinyl-1-hexenylphosphonic acids. A dimer, potential precursor of acyclic polynucleotides (APN), homomorphous with DNA, was also prepared.
    Materialart: Digitale Medien
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  • 194
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 955-958 
    ISSN: 1434-193X
    Schlagwort(e): Tetraethylammonium peroxydicarbonate ; Tetraethylammonium carbonate ; N-alkylated pyrroles ; Electrochemistry ; Electrogenerated bases ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Electrochemically generated tetraethylammonium peroxydicarbonate (TEAPC) and tetraethylammonium carbonate (TEAC) react under very mild conditions with pyrroles affording, after addition of a suitable alkylating agent, the corresponding N-alkylated pyrroles in high yields. C-Alkylated pyrroles have not been isolated in any case reported.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
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  • 195
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 979-980 
    ISSN: 1434-193X
    Schlagwort(e): Ketones ; Myxobacterium ; Pheromones ; Stigmatellaaurantiaca ; Stigmolone ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The racemic myxobacterial pheromone (±)-1 (stigmolone), which induces the formation of the fruiting body of Stigmatellaaurantiaca, was synthesized from methyl isobutyl ketone (2) in 48% overall yield in four steps
    Materialart: Digitale Medien
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  • 196
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1005-1009 
    ISSN: 1434-193X
    Schlagwort(e): Hydrogen migration ; Anthronylidene ; Quinone methide ; Matrix isolation ; Photochemistry ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The photochemistry of 4-methyl-9,10-diazoanthrone (7a) and 1,4-dimethyl-9,10-diazoanthrone (7b) was investigated in argon matrices at 10 K. Visible-light irradiation results in the formation of the anthronylidenes 5a and b, respectively, which were identified by oxygen trapping, by comparison of the IR and UV/Vis spectra with that of the parent anthronylidene 6, and by comparison of the IR spectrum with that calculated by DFT methods. The carbenes 5 are thermally stable under the conditions of matrix isolation; however, irradiation with visible or UV light results in the rearrangement to the quinone methides 10a and b.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
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  • 197
    ISSN: 1434-193X
    Schlagwort(e): Sulfoximines ; Oxabicyclic ethers ; Asymmetric synthesis ; Euglobal ; Arenaran ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -2-Cyclopentenyl- and 2-cyclohexenylmethyl sulfoximines can be converted into angular carbon-functionalised, highly substituted, isomerically pure (ds ≥ 98%) 2-oxabicyclo[3.3.0]octanes and 2-oxabicyclo[3.4.0]nonanes in high yields by a convenient one-pot sequence. Molecular frameworks such as these can be found in many biologically active natural products. In addition to the methodological work, we report on studies towards the total synthesis of the euglobals G1 and G2 and arenaran A.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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  • 198
    ISSN: 1434-193X
    Schlagwort(e): Phosphaalkynes ; Cycloadditions ; Polycycles ; Cage compounds ; λ3-Phosphinines ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -Phosphaalkynes 2 and electron-deficient alkynes 11 readily react in a [4 + 2] cycloaddition process with 5,8-bis(trimethylsilyl)cycloocta-1,3,6-triene (8) in its bicyclic form 10 to furnish regioselectively the tricyclodecadienes 12 and 13, respectively. The phosphorus-containing compounds 12 exhibit structural features which make them suitable for homo-Diels-Alder reactions with electron-deficient acetylenes. A single crystal structure analysis of the homo-Diels-Alder adduct 14b confirmed the structure and relative configuration of the phophatricyclodecadienes 12. In solution the tricyclodecadienes 13 are prone to facile cycloreversion yielding the phthalic esters 15 and the cyclobutene 16. The latter is rapidly converted into the corresponding 1,3-butadiene 18, which can be trapped in a Diels-Alder/phospha-ene/Diels-Alder tandem reaction sequence by phosphaalkyne 2a. The phosphatricyclodecadiene 12 is thermally more stable; loss of cyclobutene 16 only occurs under FVP conditions to afford the λ3-phosphinine 22.
    Zusätzliches Material: 1 Ill.
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  • 199
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1099-1105 
    ISSN: 1434-193X
    Schlagwort(e): Asymmetric synthesis ; Chiral synthons ; P-(o-Hydroxyaryl)diazaphospholidine P-oxides ; Rearrangements ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -The totally regio- and stereoselective P-O-to-P-C rearrangement in the synthesis of various chiral P-(o-hydroxyaryl)diazaphospholidine P-oxides has been investigated. This reaction proceeds with excellent yields ranging from 72 to 92%, total retention of configuration at the phosphorus atom, and complete regioselectivity. An exception was found with naphthyl derivatives, which gave mixtures of two regioisomers. In all cases, the products generated have been unambiguously characterized by 1H-, 13C-, and 31P-NMR spectroscopy as well as by X-ray-diffraction analysis.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
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  • 200
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1137-1141 
    ISSN: 1434-193X
    Schlagwort(e): Cyclocarbonylation ; Alkynes ; Catalysis ; Palladium ; Vinyl triflates ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -o-Ethynylphenols react with vinyl triflates, in the presence of tetrakis(triphenylphosphane)palladium(0) and under carbon monoxide, to form 3-alkylidene-2-coumaranones in good yield.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
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