A21978C, A COMPLEX OF NEW ACIDIC PEPTIDE ANTIBIOTICS - ISOLATION, CHEMISTRY, AND MASS-SPECTRAL STRUCTURE ELUCIDATION
A21978C, A COMPLEX OF NEW ACIDIC PEPTIDE ANTIBIOTICS - ISOLATION, CHEMISTRY, AND MASS-SPECTRAL STRUCTURE ELUCIDATION
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DOI：
10.7164/antibiotics.40.761
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发表时间：
1987-06-01
影响因子：
3.3
通讯作者：
HERLIHY, WC
中科院分区：
文献类型：
--
作者：
DEBONO, M;BARNHART, M;HERLIHY, WC
A21978 C是由玫瑰孢链霉菌NRRL 11379产生的一种新型酸性脂肽类抗生素复合物，对革兰氏阳性菌有抑制作用。从纯化的复合物中HPLC分离各种组分导致分离A21978 C1、-C2和-C3（主要组分）和-C4、-C5和-C6（次要组分）。将这些组分中的每一种与犹他游动放线菌（NRRL 12052）的培养物一起发酵，通过从N-末端除去脂肪酸酰基得到相同的无活性肽（“A21978 C核”）。该肽由13个氨基酸组成：L-犬尿氨酸、L-苏型-3-甲基谷氨酸、L-天冬酰胺、L-天冬氨酸（3个残基）、甘氨酸（2个残基）、L-色氨酸、L-鸟氨酸、D-丙氨酸、D-丝氨酸和L-苏氨酸。使用Edman降解和气相色谱质谱（GC-MS）分析从部分水解获得的适当衍生化肽的组合测定氨基酸序列。每个主要成分被证明是酰化的支链脂肪酸在N-末端和这种脂肪酸的结构，通过1H NMR和质谱方法确定。根据该降解和理化信息，指定了A21978 C的结构。
A21978C, produced by Streptomyces roseosporus, NRRL 11379, is a complex of new acidic lipopeptolide antibiotics which inhibits Gram-positive bacteria. HPLC separation of the various components from the purified complex resulted in the isolation of A21978C1, -C2 and -C3 (major components) and -C4, -C5 and -C6 (minor components). Each of these components was fermented with cultures of Actinoplanes utahensis (NRRL 12052) to give the identical inactive peptide ("A21978C nucleus") by removal of the fatty acid acyl groups from the N-terminus. This peptide was composed of 13 amino acids: L-kynurenine, L-threo-3-methylglutamic acid, L-asparagine, L-aspartic acid (3 residues), glycine (2 residues), L-tryptophan, L-ornithine, D-alanine, D-serine and L-threonine. The amino acid sequence was determined using a combination of the Edman degradation and gas chromatography mass spectrum (GC-MS) analysis of appropriately derivatized peptides obtained from partial hydrolysis. Each major component was shown to be acylated with a branched chain fatty acid at the N-terminus and the structure of this fatty acid was determined by 1H NMR and mass spectral methods. A structure for A21978C was assigned on the basis of this degradative and physico-chemical information.