八肽菌素D的结构（芽孢杆菌属抗生素的研究。第二十八篇）

The structure of octapeptin D (studies on antibiotics from the genus Bacillus. XXVIII).

作者信息

Kato T, Shoji T

出版信息

J Antibiot (Tokyo). 1980 Feb;33(2):186-91. doi: 10.7164/antibiotics.33.186.

DOI:10.7164/antibiotics.33.186

Abstract

Amino acid analysis of the acid hydrolyzate of octapeptin D revealed the amino acid composition. These amino acids were converted to L-leucyl-derivatives and analyzed by high performance liquid chromatography to clarify their chiralities. These were determined to be: 2,4-diaminobutyric acid (4L), Ser (D), Leu (2L, 1D). Deacylation with polymyxin acylase afforded deacyl octapeptin D. EDMAN degradation on deacyl octapeptin D revealed the N-terminal amino acid. Application of the chemical cleavage reaction for fragmentation of seryl peptides on tri (DNP)-octapeptin D afforded a DNP-heptapeptide, whose sequence was clarified by EDMAN degradation. Octapeptin D was separated into four components (D1,D2,D3 and D4) by high performance liquid chromatography. All the components were examined for their amino acid and fatty acid compositions. From the results, the structures of octapeptins D1, D2, D3 and D4 were determined.

摘要

对八肽菌素D的酸水解产物进行氨基酸分析，得出了氨基酸组成。这些氨基酸被转化为L-亮氨酰衍生物，并通过高效液相色谱进行分析，以阐明它们的手性。结果确定为：2,4-二氨基丁酸（4L）、丝氨酸（D）、亮氨酸（2L，1D）。用多粘菌素酰基转移酶进行脱酰基反应得到脱酰基八肽菌素D。对脱酰基八肽菌素D进行埃德曼降解，揭示了N端氨基酸。对三（二硝基苯基）-八肽菌素D应用丝氨酰肽片段化的化学裂解反应，得到一个二硝基苯基七肽，其序列通过埃德曼降解得以阐明。八肽菌素D通过高效液相色谱分离为四个组分（D1、D2、D3和D4）。对所有组分进行了氨基酸和脂肪酸组成分析。根据结果，确定了八肽菌素D1、D2、D3和D4的结构。