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

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Reductase of Mutanobactin Synthetase Triggers Sequential C-C Macrocyclization, C-S Bond Formation, and C-C Bond Cleavage.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-09 , DOI: 10.1021/acs.orglett.9b04501
Min Wang _{1,

2,

3} , Zhoujie Xie ₁ , Shoubin Tang ₂ , Ee Ling Chang ₂ , Yue Tang _{1,

2,

3} , Zhengyan Guo _{1,

3} , Yinglu Cui ₁ , Bian Wu _{1,

3} , Tao Ye ₂ , Yihua Chen _{1,

3}

Affiliation

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.

中文翻译：

变菌素合成酶的还原酶触发顺序的CC大环化，CS键形成和CC键裂解。

含有大环和/或硫氮杂环丁烷的变菌素（MUB）及其同类物是来自变形链球菌（龋齿的主要病因）的脂肽。在这里，我们显示MubD的C末端还原酶结构域以醛形式释放脂六肽中间体，这使CC能够自发地大环化。在存在巯基的情况下，大环化的MUB可以进一步自发形成CS键和CC键断裂，从而生成各种MUB同系物。

更新日期：2020-01-10

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