Indole methylation protects diketopiperazine configuration in the maremycin biosynthetic pathway

The maremycin biosynthetic gene cluster has been identified in Streptomyces sp. B9173. Comparative metabolic profiling with knockout mutant strains led to the identification of new products correlated to the maremycin biosynthesis, in particular the ＂demethyl＂-maremycins with an unexpected D-tryptop...

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Published inScience China. Chemistry Vol. 59; no. 9; pp. 1224 - 1228
Main Authors Lan, Yingxia, Zou, Yi, Huang, Tingting, Wang, Xiaozheng, Brock, Nelson L., Deng, Zixin, Lin, Shuangjun
Format Journal Article
LanguageEnglish
Published Beijing Science China Press 01.09.2016
Springer Nature B.V
Subjects
Biosynthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Communications
D-色氨酸
Tryptophan
保护
吲哚
哌嗪
生物合成基因簇
生物合成途径
甲基化
配置
maremycin
methyltransferase
epimerization
methylation
biosynthesis
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Summary:The maremycin biosynthetic gene cluster has been identified in Streptomyces sp. B9173. Comparative metabolic profiling with knockout mutant strains led to the identification of new products correlated to the maremycin biosynthesis, in particular the ＂demethyl＂-maremycins with an unexpected D-tryptophan unit. A biosynthetic pathway for the maremycins is proposed and plausible reasoning for tryptopban epimerization in the demethylmaremycin biosynthesis is also provided.
Bibliography:biosynthesis, maremycin, N-methylation, methyltransferase, epimerization
The maremycin biosynthetic gene cluster has been identified in Streptomyces sp. B9173. Comparative metabolic profiling with knockout mutant strains led to the identification of new products correlated to the maremycin biosynthesis, in particular the ＂demethyl＂-maremycins with an unexpected D-tryptophan unit. A biosynthetic pathway for the maremycins is proposed and plausible reasoning for tryptopban epimerization in the demethylmaremycin biosynthesis is also provided.
11-5839/O6
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-016-0026-7