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  • 1
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metabolites of Microorganisms, 1891)  -  Structure Elucidation and Partial Synthesis of the Nucleoside Antibiotic Nikkomycin BIn the culture filtrate of Streptomyces tendae, from which the nucleoside antibiotics nikkomycin Z2) (1a) and nikkomycin X3) (1b) were isolated, a third component, nikkomycin B (7), was found. This new antibiotic contains a p-hydroxyphenyl residue instead of a 3-hydroxypyridyl residue in the amino acid moiety (6). The amino acid is linked to a 5-amino hexuronic acid to which 4-formyl-4-imidazolin-2-one is bound as an N-glycoside. The structure of the new amino acid constituent could be derived by mass spectrometry and was confirmed by synthesis of a mixture of diastereomers of 2-amino-4-hydroxy-4-(p-hydroxyphenyl)-3-methylbutyric acid.
    Notes: Das Kulturfiltrat von Streptomyces tendae, aus dem die Nucleosidantibiotika Nikkomycin Z2) (1a) und Nikkomycin X3) (1b) isoliert werden konnten, lieferte noch Nikkomycin B (7), das an-stelle des 3-Hydroxypyridin-Systems von 1 einen p-Hydroxyphenyl-Rest im Aminosäurebaustein 6 enthält. Dieser ist peptidartig mit einer 5-Aminohexuronsäure verknüpft, an die 4-Formyl-4-imidazolin-2-on N-glykosidisch gebunden ist. Die Ableitung der Konstitution des neuen Aminosäurebausteins gelang durch Massenspektrometrie und Synthese eines Diastereomerengemisches der 2-Amino-4-hydroxy-4-(p-hydroxyphenyl)-3-methylbuttersäure (6). In der biologischen Aktivität ist Nikkomycin B von den genannten Vertretern dieser Gruppe nicht zu unterscheiden.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metabolites of Microorganisms, 199.  -  Structure Elucidation of the Nikkomycins I, J, M, and NNikkomycins are nucleoside antibiotics exhibiting fungicide and insecticide activity which is due to an inhibition of chitin biosynthesis. From the culture filtrate of Streptomyces tendae the previously described nikkomycins Z2) (1 a) and X3) (1 b) have been isolated as major components. As minor components the nikkomycin B4) (1 c) as well as the nikkomycins I (1 d), J (1 e), M (1 f), and N (1 g), described in this paper, have been isolated.
    Notes: Die Nikkomycine sind Nucleosidantibiotika mit fungizider und insektizider Wirkung, die auf einer Hemmung der Chitinbiosynthese beruhen. Das Kulturfiltrat von Streptomyces tendae liefert als Hauptkomponenten die bereits beschriebenen Nikkomycine Z2 (1 a) und X3) (1 b). Als Nebenkomponenten lassen sich aus dem Kulturfiltrat die Nikkomycine B4) (1 c) sowie die im folgenden beschriebenen Nikkomycine I (1 d), J (1 e), M (1 f) und N (1 g) isolieren.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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