Reductase of Mutanobactin Synthetase Triggers Sequential C-C Macrocyclization, C-S Bond Formation, and C-C Bond Cleavage
| Autor: | Zhoujie Xie, Bian Wu, Min Wang, Yinglu Cui, Ee Ling Chang, Yue Tang, Shoubin Tang, Yihua Chen, Tao Ye, Zhengyan Guo |
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| Rok vydání: | 2020 |
| Předmět: |
Stereochemistry
Stereoisomerism Reductase 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Aldehyde Peptides Cyclic Lipopeptides Molecule Physical and Theoretical Chemistry Bond cleavage chemistry.chemical_classification biology Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Bond formation biology.organism_classification Streptococcus mutans 0104 chemical sciences Cyclization Oxidoreductases |
| Zdroj: | Organic letters. 22(3) |
| ISSN: | 1523-7052 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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