title: Goadsporin, a chemical substance which promotes secondary metabolism and Morphogenesis in streptomycetes. II. Structure determination.
abstract: The structure of goadsporin was determined by using spectroscopic techniques. NMR analysis revealed that goadsporin consists of 19 amino acids, two of which are dehydroalanines (Deala), and six of which are cyclized to oxazoles (Oxz) and thiazoles (Thz) by dehydrative cyclization and dehydrogenation from serine, threonine and cysteine. NMR analysis established seven partial structures, and their sequence was determined by CID-MS/MS. Negative mode FAB-MS/MS gave product ions arising from charge-remote fragmentation that allowed determination of the sequence of the amino acid components as AcNH-Ala-MeOxz-Val-Deala-MeOxz-Ile-Leu-Thz-Ser-Gly-Gly-MeOxz-Leu-Deala-Oxz-Ala-Gly-Thz-Val-OH. The chiral amino acids were determined by the advanced Marfey's method to have L-configurations.
authors.affiliation: Biotechnology Research Center, Toyama Prefectural University, Kosugi, Japan. yas@pu-toyama.ac.jp
authors.forename: Y
authors.initials: Y
authors.lastname: Igarashi
authors.forename: Y
authors.initials: Y
authors.lastname: Kan
authors.forename: K
authors.initials: K
authors.lastname: Fujii
authors.forename: T
authors.initials: T
authors.lastname: Fujita
authors.forename: K
authors.initials: K
authors.lastname: Harada
authors.forename: H
authors.initials: H
authors.lastname: Naoki
authors.forename: H
authors.initials: H
authors.lastname: Tabata
authors.forename: H
authors.initials: H
authors.lastname: Onaka
authors.forename: T
authors.initials: T
authors.lastname: Furumai
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D036341:Intercellular Signaling Peptides and Proteins; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; C449027:goadsporin