BIOSYNTHESIS OF DYNEMICIN-A, A 3-ENE-1,5-DIYNE ANTITUMOR ANTIBIOTIC
BIOSYNTHESIS OF DYNEMICIN-A, A 3-ENE-1,5-DIYNE ANTITUMOR ANTIBIOTIC
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DOI：
10.1021/ja00037a011
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发表时间：
1992-05-20
影响因子：
15
通讯作者：
IWASAKI, S
中科院分区：
文献类型：
--
作者：
TOKIWA, Y;MIYOSHISAITOH, M;IWASAKI, S
利用小单孢菌（Micromonospora chersina）M956-1对动力霉素A（DNM-A）的生物合成进行了研究。结果表明，该化合物是由两个heptaketide链生物合成的，这两个链分别形成双环烯二炔核心和蒽醌部分;两者都衍生自七个头-尾偶联的乙酸酯单元，而羧基衍生自乙酸酯单元的一个碳，O-甲基衍生自甲硫氨酸。未观察到甘氨酸的完整掺入，但碳被掺入O-甲基中。埃培霉素/加利车霉素类抗生素中相关的C-15烯二炔环骨架可以类似地衍生为动力霉素A的烯二炔核心，但新制癌素生色团A的C-14环状碳酸酯/双环[7.3.0]十二碳二烯二炔环系统似乎是通过稍微不同的过程生物合成的。
Biosynthetic studies of dynemicin A (DNM-A) were carried out by examining the incorporation of singly and doubly C-13-labeled acetates, [methyl-C-13]methionine and [N-15,2-C-13]glycine, into DNM-A by cultures of Micromonospora chersina M956-1. Thc results show that the compound is biosynthesized from two heptaketide chains, which form the bicyclic enediyne core and the anthraquinone moiety, respectively; both are derived from seven head-to-tail coupled acetate units, while the carboxyl group is derived from one carbon of an acetate unit and the O-methyl group from methionine. Intact incorporation of glycine was not observed, but a carbon was incorporated into the O-methyl group. The related C-15 enediyne ring skeletons in the esperamicin/calicheamicin class of antibiotics may be similarly derived as the enediyne core of dynemicin A, but the C-14 cyclic carbonate/bicyclo[7.3.0]dodecadienediyne ring system of neocarzinostatin chromophore A appears to be biosynthesized via a somewhat different process.