The Novel Gluconeogenesis Inhibitors FR225659 and FR225656 from Helicomyces sp. No. 19353: III. Structure Determination

During the course of screening for novel gluconeogenesis inhibitors, FR225659 and its related compounds were isolated from a fermentation broth of Helicomyces sp. No. 19353. Spectroscopic analysis concluded that FR225659 is an N-acyl tripeptide consisting of a novel acyl, a 3-chloro-4-hydroxyarginin...

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Bibliographic Details
Published in:Journal of antibiotics 2003/08/25, Vol.56(8), pp.694-699
Main Authors: ZENKOH, TATSUYA, OHTSU, YOSHIHIRO, YOSHIMURA, SEIJI, SHIGEMATSU, NOBUHARU, TAKASE, SHIGEHIRO, HINO, MOTOHIRO
Format: Article
Language:English
Subjects:
Biological and medical sciences
General and cellular metabolism. Vitamins
Gluconeogenesis - drug effects
Hypoglycemic Agents - chemistry
Hypoglycemic Agents - pharmacology
Medical sciences
Oligopeptides - chemistry
Oligopeptides - pharmacology
Pharmacology. Drug treatments
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Summary:During the course of screening for novel gluconeogenesis inhibitors, FR225659 and its related compounds were isolated from a fermentation broth of Helicomyces sp. No. 19353. Spectroscopic analysis concluded that FR225659 is an N-acyl tripeptide consisting of a novel acyl, a 3-chloro-4-hydroxyarginine, a 3-hydroxy-3-methylproline and a dehydrovaline. Degradation study allowed assignment of the absolute configuration of the 3-hydroxy-3-methylproline to be (2S, 3R). FR225656 was shown to possess a dehydroisoleucine instead of the dehydrovaline of FR225659.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.56.694