On the regioselectivity of thioether formation by lacticin 481 synthetase

Xingang Zhang; Weijuan Ni; Wilfred A. Van Der Donk

doi:10.1021/ol071301h

On the regioselectivity of thioether formation by lacticin 481 synthetase

Xingang Zhang, Weijuan Ni, Wilfred A. Van Der Donk

Research output: Contribution to journal › Article › peer-review

Abstract

Lantibiotic synthetases generate intramolecular thioether cross-links within peptides through the Michael-type addition of cysteines onto dehydroamino acids originating from Ser and Thr. Presented here is an assay that readily distinguishes between enzymatic and nonenzymatic formation of these cross-links. The results demonstrate unequivocally that lacticin 481 synthetase can generate non-native thioether cross-links.

Original language	English (US)
Pages (from-to)	3343-3346
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	17
DOIs	https://doi.org/10.1021/ol071301h
State	Published - Aug 16 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol071301h

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abstract = "Lantibiotic synthetases generate intramolecular thioether cross-links within peptides through the Michael-type addition of cysteines onto dehydroamino acids originating from Ser and Thr. Presented here is an assay that readily distinguishes between enzymatic and nonenzymatic formation of these cross-links. The results demonstrate unequivocally that lacticin 481 synthetase can generate non-native thioether cross-links.",

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AB - Lantibiotic synthetases generate intramolecular thioether cross-links within peptides through the Michael-type addition of cysteines onto dehydroamino acids originating from Ser and Thr. Presented here is an assay that readily distinguishes between enzymatic and nonenzymatic formation of these cross-links. The results demonstrate unequivocally that lacticin 481 synthetase can generate non-native thioether cross-links.

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On the regioselectivity of thioether formation by lacticin 481 synthetase

Abstract

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