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  • Chemistry  (21)
  • 1985-1989  (21)
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  • 1
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen. 253. Mitteilung252, Mitteilung. Hormaomycin, ein neues Peptid-lacton mit morphogener Aktivität auf Streptomyceten (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 426-437 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hormaomycin, a Novel Peptide Lactone with Morphogenetic Activity on StreptomycesA culture identified as Streptomyces griseoflavus (strain W-384) has been found to produce a novel peptide-lactone antibiotic designated hormaomycin (6). The empirical molecular formula of the compound is established to be C55H69ClN10O14. The constituent amino acids of the antibiotic are suggested to be allothreonine (1; 1), isoleucine (2; 1), 3-methyl-phenylalanine (3; 2), and, for the first time identified from a natural source, 4-[(Z)-prop-1-enyl]-proline (4; 1) and 3-(2-nitrocyclopropyl)-alanine (5; 2). The amino acids were delivered by acidic hydrolysis and assigned by high-resolution- GC/MS analysis (after transformation to derivatives) in combination with extended 2D-NMR experiments of the antibiotic itself. From the latter, it became plausible that the N-terminus of the peptide chain is acylated by a Cl-containing derivative of 1H-pyrrol-2-carboxylic acid. Hormaomycin is active against some Gram-positive bacteria. In addition, the antibiotic exhibits potent aerial mycelium-inducing activity and effects the production of antibiotics.
    Notes: No abstract.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720303
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  • 2
    Electronic Resource
    Electronic Resource
    Sequence and Conformation of Suzukacillin A (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1041-1062 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Sequenz und Konformation von Suzukacillin ADie Sequenz des spannungsabhängige Membranporen bildenden Polypeptidantibiotikums Suzukacillin A wurde bestimmt durch eine Kombination von trifluoracetolytischer Spaltung, präparativer Isolierung von Fragmenten und Analyse durch Gaschromatographie - Massenspektrometrie sowie Felddesorptions- und Fast-Atom-Bombardment-Massenspektrometrie. Suzukacillin A ist ein mikroheterogenes Eikosapeptidantibiotikum (Ac-Aib-L-Ala-Aib-Ala-Aib-Ala(Aib)-Gln-Aib-Aib(Leu)-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib(D-Iva)-Gln-Gln-Phl) mit einer Sequenz, einer α-helicalen Konformation (nach13C-NMR- und Circulardichroismus-Messungen) und membranmodifizierenden Eigenschaften, die dem Alamethicin ähnlich sind.
    Notes: The sequence of the potential-dependent membrane pore-forming polypeptide antibiotic suzukacillin A was determined by a combination of trifluoroacetolytic cleavage, preparative isolation of fragments, and analysis by gas chromatography - mass spectrometry, field-desorption and fast-atom bombardment mass spectrometry. Suzukacillin A is a microheterogeneous eicosapeptide antibiotic (Ac-Aib-L-Ala-Aib-Ala-Aib-Ala(Aib)-Gln-Aib-Aib(Leu)-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib(D-Iva)-Gln-Gln-Phl) with a sequence, an α-helical conformation (according to 13C NMR and circular dichroism), and membrane-modifying properties related to alamethicin.
    Additional Material: 13 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850518
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  • 3
    Electronic Resource
    Electronic Resource
    Synthese reiner Stereoisomerer der N-terminalen Aminosäure von Nikkomycin B (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 2165-2177 
    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 Pure Stereoisomers of the N-terminal Amino Acid of Nikkomycin BPure stereoisomers of 2-amino-4-hydroxy-4-(p-hydroxyphenyl)-3-methylbutanoic acid (8c), the N-terminal amino acid of nikkomycin B (10a, b), were synthesized by 1,3-dipolar cycloaddition of (ethoxycarbonyl)methanenitrile oxide (2) to the olefines 1, separation of the diastereomeric 4,5-dihydro-3-isoxazolecarboxamides 6, and diastereoselective reductive cleavage and hydrolysis of 6. X-ray structure analysis revealed the absolute configuration (2R,3R,4R) for one pure synthetic stereoisomer of 8c. Gas chromatography on a chiral stationary phase and 1H NMR enabled us to assign the (2S,3S,4S) configuration to the natural amino acid.
    Notes: Reine Stereoisomere von 2-Amino-4-hydroxy-4-(p-hydroxyphenyl)-3-methylbuttersäure (8c), der N-terminalen Aminosäure von Nikkomycin B (10a, b), wurden nach 1,3-dipolarer Cycloaddition von (Ethoxycarbonyl)methannitriloxid (2) an die Olefine 1 und Trennung der diastereomeren 4,5-Dihydro-3-isoxazolcarboxamide 6 durch diastereoselektive reduktive Spaltung und Verseifung von 6 hergestellt. Mit Hilfe eines reinen, synthetischen Stereoisomers von 8c, dessen absolute Konfiguration (2R,3R,4R) durch Kristallstrukturanalyse bestimmt werden konnte, sowie mit Hilfe von Gaschromatographie an chiraler Phase und 1H-NMR gelang es, der natürlichen Aminosäure die Konfiguration (2S,3S,4S) zuzuordnen.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519851107
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  • 4
    Electronic Resource
    Electronic Resource
    The C-Terminal Heptapeptides of Suzukacillin A and Alamethicin F30  -  Sequence, Conformation, and Synthesis (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 365-377 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Die C-terminalen Heptapeptide von Suzukacillin A und Alamethicin F30  -  Sequenz, Konformation und SyntheseWährend der Sequenzierung des membranmodifizierenden Eikosapeptidantibiotikums Suzukacillin A wurden zwei C-terminale Heptapeptide durch selektive Trifluoracetolyse erhalten: L-Pro-L-Val-Aib-D-Iva-L-Gln-L-Phl und L-Pro-L-Val-Aib-Aib-L-Gln-L-Gln-L-Phl. Der chromatographische und spektroskopische Vergleich (FAB-MS, FD-MS, 13C-NMR, CD, UV) dieser isolierten natürlichen Fragmente mit dem synthetischen Segment L-Pro-L-Val-Aib-Aib-L-Gln-L-Gln-L-Phl (2) und dem synthetischen C-terminalen Segment von Alamethicin F30 L-Pro-L-Val-Aib-Aib-L-Glu-L-Gln-L-Phl (1) beweist die Sequenz 14-20 von Suzukacillin A.
    Notes: During the sequencing of the membrane-modifying eicosapeptide antibiotic suzukacillin A two C-terminal heptapeptides were obtained via selective trifluoroacetolysis: L-Pro-L-Val-Aib-D-Iva-L-Gln-L-Gln-L-Phl and -Pro-L-Val-Aib-Aib-L-Gln-L-Phl. The chromatographic and spectroscopic comparison (FAB MS, FD MS, 13C NMR, CD, UV) of these isolated natural fragments with the synthetic segment L-Pro-L-Val-Aib-Aib-L-Gln-L-Gln-L-Phl (2) and the synthetic C-terminal segment of alamethicin F30 L-Pro-L-Val-Aib-Aib-L-Glu-L-Gln-L-Phl (1) proved the sequence 14-20 of suzukacillin A.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850212
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  • 5
    Electronic Resource
    Electronic Resource
    Drei neue Aminosäuren aus dem Nikkomycin-Komplex  -  Strukturaufklärung und Synthese (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 407-421 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Three Novel Amino Acids from the Nikkomycin Complex - Structure Elucidation and SynthesisFrom the culture medium of Streptomyces tendae Tue 901 some new metabolites were characterized: 2-amino-4-hydroxy-3-methyl-4-(2-pyridyl)butanoic acid (1) [nikkomycin E], its isomer 2-amino-4-hydroxy-3-methyl-4-(3-pyridyl)butanoic acid (2) [as N-terminal constituent of the nikkomycins Px (5) and Rz (6)], and 2-amino-4-hydroxy-4-(2-pyridyl)butanoic acid (3) [as N-terminal amino acid of the nikkomycins Kx (7) and Kz (8)]. The structure elucidation was achieved by NMR, mass spectrometry and by comparison with synthetic reference compounds.
    Notes: Aus dem Kulturfiltrat von Streptomyces tendae Tue 901 wurden weitere neue Metabolite charakterisiert: 2-Amino-4-hydroxy-3-methyl-4-(2-pyridyl)buttersäure (1) [Nikkomycin E], die dazu isomere 2-Amino-4-hydroxy-3-methyl-4-(3-pyridyl)buttersäure (2) [als N-terminaler Baustein der Nikkomycine Px (5) und Rz (6)] und 2-Amino-4-hydroxy-4-(2-pyridyl)buttersäure (3) [als N-terminale Aminosäure der Nikkomycine Kx (7) und Kz (8)]. Die Strukturaufklärung erfolgte durch Kernresonanz, Massenspektrometrie und durch Vergleich mit entsprechenden Syntheseprodukten.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860301
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  • 6
    Electronic Resource
    Electronic Resource
    Partialsynthese der Nikkomycine Bx und Kx sowie unnatürlicher Stereoisomerer und Strukturanaloga (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 803-807 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Partial Synthesis of Nikkomycins Bx, Kx and Unnatural Stereoisomers and Structural AnaloguesNikkomycin Bx (8a) was prepared by connecting synthetic (2S,3S,4S)-2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methyl-butanoic acid (1a) to natural 1-(5′-amino-5-deoxy-β-D-allofuranuronosyl)-4-formyl-1H-imidazol-2(3H)-one (6a). In an analogous way the (2S,3R,4R)-stereoisomer 8b, the p-methoxy derivative 8c, nikkomycin Kx (8d), and its analogues 8e and 8f, as well as the nikkomycin Z analogues 8g and 8h were prepared. Of the synthetic products only the stereoisomers 8a and 8d, corresponding to the natural products, showed the expected fungicidal activity. The p-methoxyphenyl derivative 8c is only active against yeasts, while the nikkomycin analogues 8e-8h are inactive against fungi.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870832
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  • 7
    Electronic Resource
    Electronic Resource
    Structure Elucidation of the Peptide Antibiotics Herbicolin A and B (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 2285-2300 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Strukturaufklärung der Peptidantibiotika Herbicolin A und BDie Struktur der amphiphilen Peptidantibiotika Herbicolin A und B konnte mit physikalischen Methoden sowie durch chemischen Abbau und Partialsynthesen identifiziert werden. Herbicolin B ist ein Lipodepsipeptid der Sequenz DH-Abu-L-Thr-D-aThr-D-Leu-Gly-D-Gln-Gly-N-Me-L-aThr-L-Arg (DH-Abu = 2,3-Dehydro-α-aminobuttersäure), dessen C-terminaler Argininrest mit der Hydroxygruppe von L-Thr lactonisiert und dessen N-Terminus durch (R)-3-Hydroxytetradecansäure acyliert ist. In der Hauptkomponente Herbicolin A ist im Unterschied zu Herbicolin B zusätzlich ein Molekül D-Glucose 1-α-glycosidisch mit der 3-Hydroxytetradecansäure verknüpft. Somit ist Herbicolin A das erste bekannte Glycolipodepsinonapeptid-Antibiotikum.
    Notes: The structures of the amphiphilic peptide antibiotics herbicolin A and B were determined by application of physical methods, chemical degradation, and partial syntheses. Herbicolin B is a lipodepsinonapeptide with the sequence DH-Abu-L-Thr-D-aThr-D-Leu-Gly-D-Gln-Gly-N-Me-L-aThr-L-Arg (DH-Abu = 2,3-dehydro-α-aminobutyric acid). The C-terminal Arg residue forms a lactone ring with the hydroxy group of L-Thr, while the N-terminus is acylated by an (R)-3-hydroxytetradecanoic acid residue. The main component herbicolin A differs from herbicolin B in an additional D-glucose moiety linked in an 1-α-glycosidic bond to the 3-hydroxytetradecanoic acid residue. Thus herbicolin A constitutes the first glycolipodepsinonapeptide antibiotic known so far.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519851117
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  • 8
    Electronic Resource
    Electronic Resource
    Epoxytetrahydroedulan, a New Terpenoid from the Hairpencils of Euploea (Lep.: Danainae) Butterflies (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1195-1201 
    Details
    ISSN: 0170-2041
    Keywords: Euploea ; Danainae ; Butterflies, hairpencils ; Terpenoids ; Edulan ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Epoxytetrahydroedulan, ein neues Terpenoid aus den Haarpinseln der Schmetterlinge Euploea (Lep.: Danainae)Die Hauptkomponente der flüchtigen Inhaltsstoffe der Haarpinsel männlicher Schmetterlinge der Gattung Euploea (Danainae) wurde als 9,10-Epoxytetrahydroedulan identifiziert: 1R,2S,4S,7R,10S)-1,6,6,10-Tetramethyl-
    Notes: The main component among the volatiles from hairpencils of male danaid butterflies of the genus Euploea was found to be 9,10-epoxytetrahydroedulan: (1R,2S,4S,7R, 10S)-1,6,6,10-tetramethyl-3,11-dioxatricyclo[5.4.0.02,4]undecane (12). Identification and synthesis of the compound are described. Another edulan derivative, (1R,3S,6R)-1,3,7,7-tetramethyl-2-oxabicyclo[4.4.0]dec-9-en-8-one (13) could be identified from the hairpencils of Danaus plexippus males.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890291
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  • 9
    Electronic Resource
    Electronic Resource
    Optisch aktives Isopren(tricarbonyl)eisen(0) und Methyltrimethylenmethan(tricarbonyl)eisen(0)Diese Arbeit wurde vom Fonds der Chemischen Industrie, vom Schweizerischen Nationalfonds zur Förderung der wissenschaftlichen Forschung und im Rahmen des Forschungsprojektes „Polysaccharidforschung“, Projekt-Nr. 0319134A, vom Bundesminister für Forschung und Technologie gefördert. (1989)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 101 (1989), S. 1744-1745 
    Details
    ISSN: 0044-8249
    Keywords: 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.19891011238
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  • 10
    Electronic Resource
    Electronic Resource
    Modifizierte Cyclodextrine - neue, hochenantioselektive Trennphasen für die GaschromatographieDiese Arbeit wurde im Rahmen des Forschungsprojekts „Polysaccharidforschung“, Projekt-Nr. 0319134A, vom Bundesminister für Forschung und Technologie gefördert. (1988)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 100 (1988), S. 989-990 
    Details
    ISSN: 0044-8249
    Keywords: 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.19881000729
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