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  • General Chemistry  (21)
  • biosynthesis  (4)
  • Occupational Health and Environmental Toxicology  (3)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of 3-polyprenyltoluquinols and 4-carboxy-2-polyprenylphenols by cell-free preparations of Euglena gracilis
    Amsterdam : Elsevier
    Phytochemistry 14 (1975), S. 2607-2615 
    Details
    ISSN: 0031-9422
    Keywords: 3-polyprenyltoluquinols ; 4-carboxy-2-polyprenylphenols ; Euglena gracilis ; Euglenophyceae ; biosynthesis ; intracellular distribution.
    Source: Elsevier Journal Backfiles on ScienceDirect 1907 - 2002
    Topics: Biology , Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://linkinghub.elsevier.com/retrieve/pii/0031-9422(75)85234-4
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  • 2
    Electronic Resource
    Electronic Resource
    Incorporation of shikimate and 4-(2'-carboxyphenyl)-4-oxobutyrate into phylloquinone
    Amsterdam : Elsevier
    Phytochemistry 13 (1974), S. 807-813 
    Details
    ISSN: 0031-9422
    Keywords: Gramineae ; Zea mays ; biosynthesis ; maize ; phylloquinone.
    Source: Elsevier Journal Backfiles on ScienceDirect 1907 - 2002
    Topics: Biology , Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://linkinghub.elsevier.com/retrieve/pii/S0031-9422(00)91144-0
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  • 3
    Electronic Resource
    Electronic Resource
    Biosynthesis of the chlorosulpholipids of Ochromonas danica
    Amsterdam : Elsevier
    Phytochemistry 13 (1974), S. 797-805 
    Details
    ISSN: 0031-9422
    Keywords: Ochromonadeae ; Ochromonas danica ; acetate ; biosynthesis ; chlorination. ; chlorosulpholipids ; linoleic acid ; malonate ; oleic acid ; saturated fatty acids
    Source: Elsevier Journal Backfiles on ScienceDirect 1907 - 2002
    Topics: Biology , Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://linkinghub.elsevier.com/retrieve/pii/S0031-9422(00)91143-9
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  • 4
    Electronic Resource
    Electronic Resource
    Elucidation of Factors Affecting the Electronic Structures of Magnesium(II) and Zinc(II) Tetraarylporphyrin Radical Cations (1995)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 1 (1995), S. 222-231 
    Details
    ISSN: 0947-6539
    Keywords: electronic structure ; frontier orbitals ; metalloporphyrins ; radical cations ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of magnesium and zinc tetraarylporphyrins and their porphyrinoxidized derivatives were studied by UV/Vis, ESR, and resonance Raman spectroscopy at various temperatures. The series included tetra(meta-dichlorophenyl)porphyrinatozinc (5), tetra(ortho-dichlorophenyl)porphyrinatozinc (6), tetra(ortho-difluorophenyl)porphyrinatozinc and -magnesium (9 and 10), and tetra(pentafluorophenyl)porphyrinatozinc and -magnesium (7 and 8). The radical cations (3a-10a) were isolated by chemical one-electron oxidation of their neutral precursors (3-10). Despite the structural similarity of all these radicals, their electronic ground state varied within the series. The position of the chloro groups was found to play a key role. While the radical cation of the meta-dichloro-substituted derivative 5a exhibited A2u spectroscopic features, the ortho-dichlorophenyl derivative (6a) showed A1u spectral features. Radicals of the fluoro-substituted porphyrins, especially that of 10, were found to have state-admixed (A1u/A2u) electronic structures, and the relative contributions of the two states was found to vary with temperature and to depend on the axial ligand. The results indicate that the fluoro-substituted porphyrins are primarily A2u at low temperature, even though their room temperature spectroscopic features resemble those of A1u cations. The elucidation of factors that affect the electronic structures of the radicals in the present series is helpful in providing a greater understanding of the spin-spin interactions in the intermediates of heme-dependant enzymatic reactions and their synthetic analogues.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19950010405
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  • 5
    Electronic Resource
    Electronic Resource
    Glycosyl Phosphatidylinositol (GPI) Anchor Synthesis Based on Versatile Building Blocks - Total Synthesis of a GPI Anchor of Yeast (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1153-1165 
    Details
    ISSN: 1434-193X
    Keywords: Carbohydrates ; Phospholipids ; Glycolipids ; Sphingosines ; Ceramides ; Ceramides-1-phosphates ; Glycosylation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -For the design of a synthesis of target molecule 1 the retrosynthetic analysis yielded building blocks 2-5, of which ceramide 2-phosphite derivative 2 and aminoethyl phosphite derivative 5 are known. The generation of α-glucosaminyl (1→6)inositol building block 3 was based on pseudodisaccharide 6 which was selectively benzoylated at 6b-O and then selectively benzylated at 3b-O to give 3. The synthesis of tetramannosyl building block 4 started from known ortho ester derivative 8 which was transformed into versatile mannosyl donors 13 and 18 and into acceptor 22. Reaction of 13 with 22 gave α-disaccharide 23, deacetylation and then mannosylation with 18 gave trisaccharide 25; ensuing deacetylation and mannosylation with 13 gave tetrasaccharide 27; deallylation, acetylation, regioselective removal of the anomeric O-acetyl group and treatment with CCl3CN/DBU afforded 4. Glycosylation of 3 with donor 4 led to pseudohexasaccharide 31 in high yield. Replacement of the O-acyl groups by O-benzyl groups and then exchange of the menthyloxycarbonyl group by an O-acetyl group gave 36 which enabled regioselective attachment of 2 and 5. To this end, the 6e-O-silyl group was removed and then the aminoethyl phosphate residue was attached with reagent 5 to give 38 in high yield. 1a-O-Deacetylation and then reaction with 2 afforded 40 as fully protected 1 which was liberated in two steps; treatment with acid removed all acid labile protective groups and finally catalytic hydrogenation afforded the desired GPI anchor 1 which could be fully structurally assigned.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Alteration of lacto-series glycolipid glycosyltransferase activities in human colonic adenocarcinoma DLD-1 cells after culture in N,N-dimethylformamide-containing medium (1990)
    New York, N.Y. : Wiley-Blackwell
    Journal of Cellular Biochemistry 44 (1990), S. 93-105 
    Details
    ISSN: 0730-2312
    Keywords: β1→3N-acetylglucosaminyltransferase ; cancer-associated carbohydrate antigens ; biosynthesis ; glycosphingolipid ; Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: Human colonic adenocarcinoma DLD-1 cells were grown under conditions which induce characteristics of differentiated cells using medium containing 0.8% N,N-dimethylformamide in order to study alterations in glycosphingolipid glycosyltransferase activities during this process. Analysis of biosynthetic reactions involved in lacto-series antigen synthesis revealed no changes in the specific activities of either β1→4galactosyltransferase or α1→3/4fucosyltransferase with N,N-dimethylformamide treatment. However, a dramatic decrease of from 14- to 20-fold in the β1→3N-acetylglucosaminyltransferase activity was observed in the treated cells. This enzyme catalyzes the rate-limiting step in lacto-series core chain synthesis. This is consistent with the pattern of regulation of lacto-series antigen expression found to occur during oncogenesis in human colonic mucosa (Holmes EH, Hakomori S, Ostrander GK: J Biol Chem 262:15649, 1987). Total glycolipids from untreated and N,N-dimethylformamide-treated cells were isolated and subjected to TLC immunostain analysis and solid phase radioimmunoassay with a series of monoclonal antibodies specific for lacto-series-based carbohydrate antigens. A decrease of about 2-fold or less in the quantity of lacto-series antigens was observed as a consequence of N,N-dimethylformamide treatment in both neutral glycolipid and ganglioside fractions. The results suggest that only very low levels of β1→3N-acetylglucosaminyltransferase activity are required for the steady state expression of significant levels of lacto-series based glycolipids and that modulation of its activity levels by N,N-dimethylformamide treatment in DLD-1 cells represents a convenient in vitro system for studying aspects of regulation of lacto-series antigen expression.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jcb.240440204
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  • 7
    Electronic Resource
    Electronic Resource
    Thermal Conversion of closo-1,2-(SiMe3)2-1,2-C2B4H4 to closo-1,6-(SiMe3)2-1,6-C2B4H4: Structure Determination by Ab Initio Calculations, Gas-Phase Electron Diffraction, and Low-Temperature X-Ray Diffraction (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1059-1063 
    Details
    ISSN: 0947-6539
    Keywords: ab initio calculations ; carboranes ; electron diffraction ; rearrangements ; structure elucidation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: closo-1,2-(SiMe3)2-1,2-C2B4H4 undergoes thermal conversion to 1,6-(SiMe3)2-1,6-C2B4H4. The reaction pathway was monitored by 11B NMR spectroscopy. The structures of the 1,2- and 1,6-isomers were optimized at the HF/6-31 G* ab initio level. Gas-phase electron diffraction studies for both isomers are reported, as well as low-temperature X-ray crystal structure determinations. Comparison of calculated structural data with the data obtained experimentally shows good agreement between theory and experiment.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030712
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  • 8
    Electronic Resource
    Electronic Resource
    Synthesis of D-erythro-Ceramide-1-phosphoinositol and Its Aminoglucosylated Derivative - Intermediates in GPI-Anchor Biosynthesis (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 291-298 
    Details
    ISSN: 1434-193X
    Keywords: Carbohydrates ; Phospholipids ; Glycolipids ; Sphingosines ; Ceramides ; Ceramide-1-phosphates ; Inositols ; Glycophosphosphingolipids, synthesis ; Glycophosphoinositol anchors ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The readily available 2,3:4,5-di-O-cyclohexylidene-D-myo-inositol derivative 3 was converted into the 1-O-unprotected D-myo-inositol derivative 6. Reaction with the phosphite derivative 7 of 3-O-tert-butyldimethylsilyl-protected ceramide furnished the target molecule D-erythro-ceramide-1-phosphoinositol (1). Reaction of O-(3,4,6-tri-O-acetyl-2-azido-β-D-glucopyranosyl)trichloroacetimidate (20) with 3 gave exclusively α(1→6)-connected glycoside 21 which was converted into the 1α-O-unprotected derivative 24. Reaction with the D-erythro-azidophytosphingosine-derived ceramide-1-phosphite derivative 17 led, after oxidation and removal of the cyanoethyl group, to protected 2-azido-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phospho-ceramide (25) which could be fully deprotected in two steps to afford the target molecule, the ceramide derivative of 2-amino-2-deoxy-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phosphate (2).
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis Of Labeled Glycosyl Phosphatidyl Inositol (GPI) Anchors (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2563-2571 
    Details
    ISSN: 1434-193X
    Keywords: Carbohydrates ; Phospholipids ; Glycolipids ; Diacylglycerolphosphates ; Glycophosphoinositol anchors ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The exploration of the molecular and structural basis for the sorting of GPI-anchored proteins is based on labeled partial structures of GPI′s which can be incorporated into the GPI anchor biosynthesis and cellular transport systems. To this end, from mannosyl donor 6 and the D-glucosaminyl-(1→6)-D-myo-inositol derivative 7 as acceptor, the pseudotrisaccharide 8 was prepared. Compound 8 was transformed into the GPI partial structures 5a,b which contain the pseudotrisaccharide ligated to two different phosphatidyl residues. Compounds 5a,b have Boc protection at the 2-amino group of the glucosamine residue (2b-position) and a free amino group at the 6b-position. The 6b-amino group was used for the ligation of the 3-(7-nitrobenzofurazan-4-yl)-aminopropanoyl group as a fluorescent label, the 5-azido-2-nitrobenzoyl and 4-azidophenylaminothiocarbonyl groups as photolabels, and the 4-azido-2-hydroxybenzoyl group as a radiolabel after the introduction of radioactive iodine by an electrophilic aromatic substitution. Thus, after acid-catalyzed removal of the protective groups, the unprotected target molecules 1-4 were obtained.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Synthese neuartiger 6-Amido-6-desoxy-L-galactose-Derivate als potente Sialyl-Lewisx-MimeticaDiese Arbeit wurde von der National Science Foundation (USA), von Sandoz Pharmaceuticals Ltd. und von der NATO (Stipendium für W. J. M.) gefördert. (1996)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 108 (1996), S. 2501-2503 
    Details
    ISSN: 0044-8249
    Keywords: Glycopeptide ; Selectine ; Sialil-Lewis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19961082009
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