短杆菌素的结构。芽孢杆菌属抗生素的研究。X。

The structure of brevistin. Studies on antibiotics from the genus Bacillus. X.

作者信息

Shoji J, Kato T

出版信息

J Antibiot (Tokyo). 1976 Apr;29(4):380-9. doi: 10.7164/antibiotics.29.380.

DOI:10.7164/antibiotics.29.380

Abstract

Acid hydrolysis revealed the constituent amino acids by brevistin as follows: aspartic acid (D-form 2, L-form 1), L-threonine (1), glycine (1), sum of L-valine and L-isoleucine (1), L-phenylalanine (1), L-trytophan (1), and 2,4-diaminobutyric acid (D-form 1, L-form 1). The constituent fatty acid was elucidated to be anteisononanoic acid by gas chromatography-mass spectrometry. A lactone linkage was proved between phenylalanine and the hydroxy group of threonine. Opening the lactone ring with dilute alkali afforded brevistinic acid. Deacylation with an enzyme preparation, Polymyxin Acylase, gave deacyl brevistinic acid. Cleavage reaction with N-bromosuccinimide, sequential analysis by EDMAN degradation and some additional evidences clarified the total structure of brevistin.

摘要

酸水解法揭示了短杆菌素的组成氨基酸如下

天冬氨酸（D型2个，L型1个）、L-苏氨酸（1个）、甘氨酸（1个）、L-缬氨酸和L-异亮氨酸之和（1个）、L-苯丙氨酸（1个）、L-色氨酸（1个）以及2,4-二氨基丁酸（D型1个，L型1个）。通过气相色谱-质谱联用仪鉴定出其组成脂肪酸为反异壬酸。已证实苯丙氨酸与苏氨酸的羟基之间存在内酯键。用稀碱打开内酯环可得到短杆菌素酸。用酶制剂多粘菌素酰基转移酶进行脱酰反应，得到脱酰短杆菌素酸。用N-溴代琥珀酰亚胺进行裂解反应、通过埃德曼降解法进行序列分析以及一些其他证据阐明了短杆菌素的完整结构。