STRUCTURE OF ALAHOPCIN (NOURSEIMYCIN), A NEW DIPEPTIDE ANTIBIOTIC

STRUCTURE OF ALAHOPCIN (NOURSEIMYCIN), A NEW DIPEPTIDE ANTIBIOTIC

The structure of alahopcin (nourseimycin) (1), a new dipeptide antibiotic isolated from Streptomyces, has been established to be (2S, 3R)-2-[(L-alanyl)amino]-4-formyl-3-(hydroxyaminocarbonyl) butyric acid. 1 exists in two cyclic hemiacetal type tautomers formed by intramolecular ring closure between...

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Veröffentlicht in:Journal of antibiotics 1985, Vol.38(3), pp.302-311
Hauptverfasser: HORII, SATOSHI, FUKASE, HIROSHI, HIGASHIDE, EIJI, YONEDA, MASAHIKO, NISHIDA, HIROYUKI, SAKAI, HEIICHI, HIROTA, AKIRA, ISOGAI, AKIRA
Format: Artikel
Sprache:eng
Schlagworte:
Analysis
Anti-Bacterial Agents
Biological and medical sciences
Chemical Phenomena
Chemistry
Dipeptides
General pharmacology
Magnetic Resonance Spectroscopy
Medical sciences
Peptides
Pharmacology. Drug treatments
Streptomyces
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Zusammenfassung:The structure of alahopcin (nourseimycin) (1), a new dipeptide antibiotic isolated from Streptomyces, has been established to be (2S, 3R)-2-[(L-alanyl)amino]-4-formyl-3-(hydroxyaminocarbonyl) butyric acid. 1 exists in two cyclic hemiacetal type tautomers formed by intramolecular ring closure between the hydroxyamino group and the formyl group in aqueous solution. The structure of the new weakly acidic amino acid (2), a constituent of 1, is revealed to be (2S, 3R)-2-amino-4-formyl-3-(hydroxyaminocarbonyl) butyric acid, and 2 also exists in two cyclic hemiacetal type tautomers in aqueous solution.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.38.302