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  • 1
    Electronic Resource
    Electronic Resource
    Allele-specific suppression of a Saccharomyces cerevisiae prp20 mutation by overexpression of a nuclear serine/threonine protein kinase (1996)
    Springer
    Molecular genetics and genomics 250 (1996), S. 614-625 
    Details
    ISSN: 1617-4623
    Keywords: Key words RCC1 ; Saccharomyces cerevisiae ; Serine/threonine protein kinase
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract  The yeast PRP20 protein is homologous to the RCC1 protein of higher eukaryotes and is required for mRNA export and maintenance of nuclear structure. RCC1/PRP20 act as guanine nucleotide exchange factors for the nuclear Ras-like Ran/GSP1 proteins. In a search for prp20-10 allele-specific high-copy-number suppressors, the KSP1 locus, encoding a serine/threonine protein kinase was isolated. Ksp1p is a nuclear protein that is not essential for vegetative growth of yeast. Inactivation of the kinase activity by a mutation affecting the catalytic center of the Ksp1p eliminated the suppressing activity. Based on the isolation of a protein kinase as a high-copy-number suppressor, the phosphorylation of Prp20p was examined. In vivo labeling experiments showed that Prp20p is a phosphoprotein; however, deletion of the KSP1 kinase did not affect Prp20p phosphorylation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02174449
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  • 2
    Electronic Resource
    Electronic Resource
    Analysis of yeast prp20 mutations and functional complementation by the human homologue RCC1, a protein involved in the control of chromosome condensation (1991)
    Springer
    Molecular genetics and genomics 227 (1991), S. 417-423 
    Details
    ISSN: 1617-4623
    Keywords: Saccharomyces cerevisiae ; mRNA metabolism ; Nucleus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Mutations in the PRP20 gene of yeast show a pleiotropic phenotype, in which both mRNA metabolism and nuclear structure are affected. srm1 mutants, defective in the same gene, influence the signal transduction pathway for the pheromone response. The yeast PRP20/SRM1 protein is highly homologous to the RCC1 protein of man, hamster and frog. In mammalian cells, this protein is a negative regulator for initiation of chromosome condensation. We report the analysis of two, independently isolated, recessive temperature-sensitive prp20 mutants. They have identical G to A transitions, leading to the alteration of a highly conserved glycine residue to glutamic acid. By immunofluorescence microscopy the PRP20 protein was localized in the nucleus. Expression of the RCC1 protein can complement the temperature-sensitive phenotype of prp20 mutants, demonstrating the functional similarity of the yeast and mammalian proteins.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00273932
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  • 3
    Electronic Resource
    Electronic Resource
    Allele-specific suppression of aSaccharomyces cerevisiae prp20 mutation by overexpression of a nuclear serine/threonine protein kinase (1996)
    Springer
    Molecular genetics and genomics 250 (1996), S. 614-625 
    Details
    ISSN: 1617-4623
    Keywords: RCC1 ; Saccharomyces cerevisiae ; Serine/threonine protein kinase
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The yeast PRP20 protein is homologous to the RCC1 protein of higher eukaryotes and is required for mRNA export and maintenance of nuclear structure. RCC1/PRP20 act as guanine nucleotide exchange factors for the nuclear Ras-like Ran/GSP1 proteins. In a search forprp20-10 allele-specific high-copy-number suppressors, theKSP1 locus, encoding a serine/threonine protein kinase was isolated. Ksp1p is a nuclear protein that is not essential for vegetative growth of yeast. Inactivation of the kinase activity by a mutation affecting the catalytic center of the Ksp1p eliminated the suppressing activity. Based on the isolation of a protein kinase as a high-copy-number suppressor, the phosphorylation of Prp20p was examined. In vivo labeling experiments showed that Prp20p is a phosphoprotein; however, deletion of the KSP1 kinase did not affect Prp20p phosphorylation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02174449
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of HR 916 B: The First Technically Feasible Route to the 1-(Pivaloyloxy)ethyl Esters of Cephalosporins (1996)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1996 (1996), S. 1735-1741 
    Details
    ISSN: 0947-3440
    Keywords: Cephalosporins ; Prodrugs ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An efficient synthesis of HR 916 B (4), the orally active 1-(RS)-(pivaloyloxy)ethyl prodrug ester of the cephalosporin cefdaloxime, was developed and applied on a multi-kg scale. AMCA (8) was prepared by exchange of the acetoxy group of fermentation product ACA (7) with the nucleophile methanol under acidic conditions. Its 7-amino group was acylated with mixed anhydride 14 to give 15. Carboxylic acid 15 was esterified with iodohydrin ester 27 or bromohydrin ester 30, respectively, to provide the acylal 16. Simultaneous removal of both the amino- and the oximo-protecting group furnished the prodrug HR 916 3, which was purified and stabilized by precipitation of its tosylate salt 4. The overall yield of 4 (ratio 5/6 = 0.65) was 39% relative to AMCA (8) (four steps), 15% relative to ACA (7) (five steps).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199619961106
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  • 5
    Electronic Resource
    Electronic Resource
    Umlagerungen vinyloger Carbonsäurechloride, XXIX 1,5-Pentadien-Sauerstoffverschiebung von (Z)-2,4,5,5-Tetrachlor-3-organylthio- und (Z,Z)-2,3,4,5-Tetrachlor-5-organylthio-2,4-pentadienthiosäure-S-estern (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 858-869 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rearrangements of Vinylogous Acyl Chlorides, XXIX1). - 1,5-Pentadiene-Oxygen Transfer of (Z)-2,4,5,5-Tetrachloro-3-organylthio- and (Z,Z)-2,3,4,5-Tetrachloro-5-organylthio-2,4-pentadienethioatesThe title compounds2 and10 are prepared from the thioates1 and from the acyl chlorides9, respectively, with thiolates in ethanol or ether. The position of the thio group in2 is determined by hydrolysis to5a and oxidation to6a which can also be obtained by oxidation of5b. On heating the thioates2a, b in boiling toluene, 1,5-pentadiene-oxygen transfer occurs to give the acyl chlorides3a,b which are characterized as amides3c, d. Acidolysis of2 leads to the 2-pyrones7 and unexpectedly to the 4-pyrones8. The mixed substituted thioates10e, f evolve an equilibrium with the thioates17e, f at 150°C by 1,5-pentadiene-oxygen transfer. The 2-pyrones18e, f are by products of this reaction. At higher temperature10a, b are pyrolized to give the 1-thiopyrones11 a, b and alkyl chlorides. Furthermore the thiolates10 are converted into the pyrylium salts15 and the 4-pyrones20.
    Notes: Die Titelverbindungen2 und10 werden aus den Thioestern1 bzw. aus den Säurechloriden9 mit Thiolaten in Ethanol oder Ether dargestellt. Die Stellung der Thiogruppe in2 wird durch Hydrolyse zu5a und Oxidation zu6a ermittelt, das auch durch Oxidation von5b erhältlich ist. In siedendem Toluol lagern sich die Thioester2a, b durch 1,5-Pentadien-Sauerstoffverschiebung in die Säurechloride3a, b um, die als Amide3c, d charakterisiert werden. Bei der Säurehydrolyse von2 entstehen neben den 2-Pyronen7 unerwartet die 4-Pyrone8. Die gemischt substituierten Thioester10e, f bilden bei 150°C durch 1,5-Pentadien-Sauerstoffverschiebung ein Gleichgewicht mit den Thioestern17e, f aus. Dabei treten die 2-Pyrone18e, f als Nebenprodukte auf. Die Thermolyse von10a, b führt unter Abspaltung von Alkylchloriden zu den 1-Thiopyronen11 a, b. Weiterhin werden die Thioester10 in die Pyryliumsalze15 und die 4-Pyrone20 übergeführt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810511
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  • 6
    Electronic Resource
    Electronic Resource
    Umlagerungen vinyloger Carbonsäurechloride, XXVI. Z,E-Isomerisierungen von 2,3,4,5-Tetrachlor-2,4-pentadienthiosäure-S-estern über 2H-Pyran-Zwischenstufen (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1960-1971 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rearrangements of Vinylogous Acyl Chlorides, XXVI1).  -  Z,E-Isomerizations of S-Alkyl and S-Aryl 2,3,4,5-Tetrachloro-2,4-pentadienethioates via 2H-Pyran IntermediatesThe (Z,Z)-thioates 2 are prepared from the acyl chlorides 1 with thiols and triethylamine in ether or with thiolates in ethanol. They are stable below 10°C. At higher temperature the alkyl esters 2a - c and 2h, i lose alkyl chloride and decompose to the 2-thiopyrones 6a, b. On heating 2 in boiling carbon tetrachloride an equilibrium with the (Z,E)-thioates 4 is set up. The state of this equilibrium depends on the substituents R and R′ but in all cases the (Z,Z)-isomers 2 are predominant. Typical reactions of 2 are the formation of pyrylium salts 7 with tin(IV) chloride and of 4-pyrone: 10 in acetic acid. 4-Pyrones 10 arise also from the aryl esters 2e - g at 140°C in addition to the 2-pyrone 9a.  -  The isolation of pyrylium salts at the temperature of the equilibrium mixture 2 = 4 (80°C) in the presence of tin(IV) chloride indicates the participation of the 2-pyran 3 as an intermediate in this equilibrium.
    Notes: Die (Z,Z)-Thioester 2 werden aus den Säurechloriden 1 mit Thiolen und Triethylamin in Ether oder mit Thiolaten in Ethanol dargestellt. Unterhalb von 100°C sind sie stabil. Bei höherer Temperatur zersetzen sich die Alkylester 2a - c und 2h, i unter Abspaltung von Alkylchlorid zu den 2-Thiopyronen 6a, b. In siedendem Tetrachlorkohlenstoff stellt sich zwischen 2 und den (Z,E)-Thioestern 4 ein Gleichgewicht ein. Die Gleichgewichtslage hängt von den Substituenten R und R′ ab, doch überwiegen in jedem Fall die (Z,Z)-Isomeren 2. Typische Reaktionen von 2 sind die Bildung der Pyryliumsalze 7 mit Zinn(IV)-chlorid und der 4-Pyrone 10 in Eisessig. 4-Pyrone 10 entstehen auch neben dem 2-Pyron 9a aus den Arylestern 2e - g bei 140°C.  -  Die Isolierung von Pyryliumsalzen bei der Temperatur der Gleichgewichtsmischung 2 = 4 (80°C) in Gegenwart von Zinn(IV)-chlorid wird als Beweis für das intermediäre Auftreten der 2-Pyrane 3 in diesem Gleichgewicht angesehen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019801206
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese antileukämischer Indolylvinyl-1-benzofurane und-benzo[b]thiophene (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 438-455 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Antileukemic Indolylvinyl-1-benzofurans and -benzo[b]thiophenes2-[2-(Indol-2-yl)vinyl]-1-benzofuran and -benzo[b]thiophene compounds 6-13 and 18-22 with terminal amidinium or imidazolinium groups were synthesized; in their antileukemic activity in mice they surpass the isosteric 2,2′-vinylenebis(1-benzofuran) and -(benzo[b]-thiophene) compounds.
    Notes: 2-[2-(Indol-2-yl)vinyl]-1-benzofuran- und -benzo[b]thiophen-Verbindungen 6-13 und 18-22 mit endständigen Amidinium- oder Imidazolinium-Gruppen wurden synthetisiert; in ihrer antileukämischen Wirksamkeit übertreffen sie bei der Maus die isosteren 2,2′-Vinylenbis(1-benzofuran)- und -(benzo[b]thiophen)-Verbindungen.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860304
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  • 8
    Electronic Resource
    Electronic Resource
    Umlagerungen vinyloger Carbonsäurechloride, XXXI. 1,5-Pentadien-Sauerstoffverschiebung von (Z)-2,3,5,5-Tetrachlor-4-phenylthio-2,4-pentadienthiosäure-S-phenylester und von (Z)-2,3,5,5-Tetrachlor-4-phenylthio-2,4-pentadienal (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 675-682 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rearrangements of Vinylogous Acyl Chlorides, XXXI1).  -  1,5-Pentadiene-Oxygen Transfer of S-Phenyl (Z)-2,3,5,5-Tetrachloro-4-phenylthio-2,4-pentadienethioate and (Z)-2,3,5,5-Tetra-chloro-4-phenylthio-2,4-pentadienalSN2′-reaction of the perchloro-substituted acid 1 with thiolates yields the stereoisomeric pentadienoic acids 3. Z-3a gives ring closure to the pyrone 4a at 180°C, while E-3a is unchanged. The mixture Z/E-3a is converted into the thioates Z- and E-6a as well as into the aldehydes Z- and E-12a. In boiling tetrachloromethane Z-6a and Z-12a rearrange into the acyl chlorides 10a and 14a, respectively, E-6a is stable up to 250°C. Z-12a in acetic acid gives the pyrone 11a, whereas E-12a does not react.
    Notes: Die perchlorsubstituierte Säure 1 liefert mit Thiolaten in einer SN2′-Reaktion die stereoisomeren Pentadiensäuren 3. Bei 180°C cyclisiert Z-3a zum Pyron 4a, während E-3a a unverändert bleibt. Aus dem Gemisch Z/E-3a werden die Thioester Z- und E-6a sowie die Aldehyde Z- und E-12a dargestellt. In siedendem Tetrachlormethan lagern sich Z-6a und Z-12a in die Säurechloride 10a bzw. 14a um. E-6a ist bis 250°C stabil. Z-12a gibt in Eisessig das Pyron 11a, wohingegen E-12a nicht reagiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820407
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  • 9
    Electronic Resource
    Electronic Resource
    Reaktionen Aromatischer Mit Aliphatischen Diazoverbindungen, II Die Azokupplung der Chinondiazide mit aliphatischen Diazoverbindungen (1959)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 623 (1959), S. 47-68 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substituierte Benzochinon-(1.2)-diazide-(2) mit ausreichender elektrophiler Aktivität kuppeln mit aliphatischen Diazoverbindungen. Unter Freisetzung ihres Stickstoffs liefern Diphenyldiazomethan und 9-Diazo-fluoren substituierte Benzo-1.3.4-oxdiazine-(2H); nur in einem Fall trat ein o-Chinon-azin als Kupplungsprodukt auf. Aus Aryl-diazomethanen gehen, je nach der Natur des Chinondiazids, Benzo-1.3.4-oxdiazine-(4H) oder -(2H) hervor. Diazoessigester oder Diazoketone ergeben die auch als cyclische Hydrazidsäureester aufzufassenden Benzo-1.3.4-oxdiazine-(4H). Benzochinon-(1.4)-diazide-(4) vereinigen sich mit Diaryl-diazomethanen zu tieffarbigen, gemischten p-Chinonazinen.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19596230106
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  • 10
    Electronic Resource
    Electronic Resource
    Umlagerungen vinyloger Carbonsäurechloride, XX. 1,5-Pentadien-Sauerstoffverschiebung bie (Z)-Perchlor-2,4-pentadienthiosäure-S-estern (1977)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 2091-2105 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rearrangements of Vinylogous Acyl Chlorides, XX. - 1,5-Oxygen Transfer of (Z)-Perchloro-2,4-pentadienethioatesS-Alkyl and S-aryl Z-perchloro-2,4-pentadienethioates 2 rearrange thermally via the pyran intermediates 3 and 4 into the 5-thiosubstituted acyl chlorides 5 by an analogous mechanism, as postulated earlier for (Z)-perchloro-2,4-pentadienones. In contrast to the irreversible rearrangement of these compounds, an equilibrium mixture 2⇋5 is formed with a pre ponderance of 5. According to this principle the thioates 2 as well as the acyl chlorides 5 may be converted into the pyrylium salts 12 in boiling tin tetrachloride. On treatment of 2 with acetic acid the same 2-pyrones 8 are obtained as by thermolysis of the acids 10 corresponding to 5.
    Notes: Die S-alkyl- und S-arylester 2 der (Z)-Perchlor-2,4-pentadienthiosäure lagern sich thermisch über die Pyranzwischenstufen 3 und 4 in die 5-thiosubstituierten Säurechloride 5 nach einem analogen Mechanismus um, wie er früher füs (Z)-Perchlor-2-4-pentadienone postuliert wurde. Im Gegensatz zur irreversiblen Umlagerung dieser Verbindungen stellt sich ein Gleichgewicht 2 ⇋ 5 ein, das aber weitgehend auf der Seite von 5 liegt. Gemäß diesem Prinzip lassen sich sowohl die Thioester 2 als auch die Säurechloride 5 in siedendem Zinn(IV)-chlorid in die Pyryliumsalze 12 überführen. Aus den Thioestern 2 entstehen in Eisessig die gleichen 2-Pyrone 8 Wei bei der Thermolyse der 5 entsprechenden Carbonsäuren 10.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197719771126
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