Biosynthesis of vineomycins A1 and B2.

N Imamura, K Kakinuma, N Ikekawa, H Tanaka, S Omura
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引用次数: 55

Abstract

Biosynthetic studies of the antibacterial and antitumor antibiotics vineomycins A1 (1) and B2 (2), produced by Streptomyces matensis subsp. vineus, were carried out by labeling experiments with [1-13C]- and [1,2-18C2]sodium acetate followed by 18C NMR spectroscopy. The results show that the benz[a]anthraquinone chromophore of 1 is derived from a decacetate metabolite with decarboxylation at the carboxyl end and that 2 is formed via C-C bond cleavage of 1. Isolation of rabelomycin from the fermentation broth of the same strain suggests a close biosynthetic relationship among the simple benz[a]anthraquinone antibiotics such as rabelomycin, tetrangomycin, aquayamycin, a C-glycosylated benz[a]anthraquinone, and vineomycins. These biosynthetic data prompted us to reconsider the previously published structure of the antibiotic SS-228Y, which has not been revised.

葡萄菌素A1和B2的生物合成。
马氏链霉菌亚种产抗菌抗肿瘤抗生素葡萄霉素A1(1)和B2(2)的生物合成研究。用[1- 13c]-和[1,2- 18c2]醋酸钠进行标记实验,然后用18C NMR谱分析。结果表明,1的苯并[a]蒽醌发色团来源于羧基端脱羧的癸乙酸代谢物,2是通过1的C-C键裂解形成的。从同一菌株的发酵液中分离出雷贝霉素,表明简单的奔驰[a]蒽醌类抗生素如雷贝霉素、四万霉素、阿卡霉素、c -糖基化奔驰[a]蒽醌和葡萄霉素之间存在密切的生物合成关系。这些生物合成数据促使我们重新考虑先前发表的抗生素SS-228Y的结构,该结构尚未修订。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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