title: The novel gluconeogenesis inhibitors FR225659 and FR225656 from Helicomyces sp. No. 19353. III. Structure determination.
abstract: 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.
authors.affiliation: Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd., 5-2-3, Tokodai, Tsukuba 300-2698, Japan.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Zenkoh
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Ohtsu
authors.forename: Seiji
authors.initials: S
authors.lastname: Yoshimura
authors.forename: Nobuharu
authors.initials: N
authors.lastname: Shigematsu
authors.forename: Shigehiro
authors.initials: S
authors.lastname: Takase
authors.forename: Motohiro
authors.initials: M
authors.lastname: Hino
mesh_terms: D005943:Gluconeogenesis / Q000187:drug effects; D007004:Hypoglycemic Agents / Q000737:chemistry* / Q000494:pharmacology; D009842:Oligopeptides / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C478489:(4-hydroxy-3-(2-(2-propenyl)-4-quinoline)benzoyl)-(3-chloro-4--hydroxyarginyl)-(3-hydroxy-3-methylprolyl)-dehydroisoleucine; C478488:(4-hydroxy-3-(2-(2-propenyl)-4-quinoline)benzoyl)-(3-chloro-4-hydroxyarginyl)-(3-hydroxy-3-methylprolyl)-dehydrovaline; D007004:Hypoglycemic Agents; D009842:Oligopeptides