Goadsporin, a chemical substance which promotes secondary metabolism and morphogenesis in streptomycetes II. Structure determination

被引：51

作者：

Igarashi, Y ^{[1
]}

Kan, Y

Fujii, K

Fujita, T

Harada, K

Naoki, H

Tabata, H

Onaka, H

Furumai, T

机构：

[1] Toyama Prefectural Univ, Biotechnol Res Ctr, Toyama 9390398, Japan

[2] Suntory Inst Bioorgan Res, Osaka 6188503, Japan

[3] Meijo Univ, Fac Pharm, Tempa Ku, Nagoya, Aichi 4688503, Japan

来源：

JOURNAL OF ANTIBIOTICS | 2001年 / 54卷 / 12期

关键词：

D O I：

10.7164/antibiotics.54.1045

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

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-DealaMeOxz-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.

引用

页码：1045 / 1053

页数：9

共 5 条

[1]

CASTRO B, 1976, SYNTHESIS-STUTTGART, P751

[2] A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: Combination of Marfey's method with mass spectrometry and its practical application [J].