多粘菌素T1的结构。（芽孢杆菌属抗生素的研究。第二十二篇）

The structure of polymyxin T1. (Studies on antibiotics from the genus Bacillus. XXII).

作者信息

Shoji J, Kato T, Hinoo H

出版信息

J Antibiot (Tokyo). 1977 Dec;30(12):1042-8. doi: 10.7164/antibiotics.30.1042.

DOI:10.7164/antibiotics.30.1042

PMID:202584

Abstract

Amino acid analysis of the acid hydrolyzate of polymyxin T1 revealed the amino acid composition. Isolation of the constituent amino acids and measurement of their optical activities clarified their chiralities. These were 2,4-diaminobutyric acid (6L), Thr(1L), Leu(2L) and Phe(1D). The constituent fatty acid was identified as anteisononanoic acid by gas chromatography and mass spectrometry. Deacylation with polymyxin acylase afforded deacyl polymyxin T. Successive EDMAN degradation on deacyl polymyxin T revealed most of its amino acid sequence. The chemical cleavage reaction for fragmentation of threonyl peptide amino acid sequence. The chemical cleavage reaction for fragmentation of threonyl peptide on penta(DNP)-polymyxin T1 cleaved it at the C-terminal side of the Thr residue to afford a DNP-octapeptide, whose sequence was clarified by EDMAN degradation. Thus, the structure of polymyxin T1 was determined.

摘要

多粘菌素T1酸水解产物的氨基酸分析揭示了其氨基酸组成。对组成氨基酸的分离及其旋光活性的测定明确了它们的手性。这些氨基酸分别是2,4-二氨基丁酸（6L）、苏氨酸（1L）、亮氨酸（2L）和苯丙氨酸（1D）。通过气相色谱和质谱法鉴定出组成脂肪酸为异壬酸。用多粘菌素酰基酶进行脱酰基反应得到脱酰基多粘菌素T。对脱酰基多粘菌素T进行连续的埃德曼降解揭示了其大部分氨基酸序列。用于苏氨酰肽氨基酸序列断裂的化学裂解反应。在五（二硝基苯基）-多粘菌素T1上对苏氨酰肽进行化学裂解反应，在苏氨酸残基的C端侧将其裂解，得到一个二硝基苯基八肽，其序列通过埃德曼降解得以阐明。因此，确定了多粘菌素T1的结构。