Reductase of Mutanobactin Synthetase Triggers Sequential C-C Macrocyclization, C-S Bond Formation, and C-C Bond Cleavage

被引：7

作者：

Wang, Min ^{[1
,2
,3
]}

Xie, Zhoujie ^{[1
]}

Tang, Shoubin ^{[3
]}

Chang, Ee Ling ^{[3
]}

Tang, Yue ^{[1
,2
,3
]}

Guo, Zhengyan ^{[2
]}

Cui, Yinglu ^{[1
]}

Wu, Bian ^{[1
,2
]}

Ye, Tao ^{[3
]}

Chen, Yihua ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Inst Microbiol, Beijing, Peoples R China

[2] Univ Chinese Acad Sci, Beijing, Peoples R China

[3] Tsinghua Univ, Shenzhen Int Grad Sch, Peking Univ, Shenzhen Grad Sch, Shenzhen, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 03期

关键词：

BIOSYNTHESIS; POLYKETIDE; CYCLIZATION; INHIBITORS; MECHANISM;

D O I：

10.1021/acs.orglett.9b04501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mutanobactins (MUBs) and their congeners that contain a macrocycle and/or a thiazepane ring are lipopeptides from Streptococcus mutans, a major causative agent of dental caries. Here we show that the C-terminal reductase domain of MubD releases the lipohexapeptide intermediates in an aldehyde form, which enables a spontaneous C-C macrocyclization. In the presence of a thiol group, the macrocyclized MUBs can further undergo spontaneous C-S bond formation and C-C bond cleavage to generate diverse MUB congeners.

引用

页码：960 / 964

页数：5

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