Mechanistic studies of the biosynthesis of 2-thiosugar: Evidence for the formation of an enzyme-bound 2-ketohexose intermediate in BexX-catalyzed reaction

Eita Sasaki; Hung Wen Liu

doi:10.1021/ja108061c

Mechanistic studies of the biosynthesis of 2-thiosugar: Evidence for the formation of an enzyme-bound 2-ketohexose intermediate in BexX-catalyzed reaction

Eita Sasaki, Hung Wen Liu

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

14 Citations (Scopus)

Abstract

The first mechanistic insight into 2-thiosugar production in an angucycline-type antibiotic, BE-7585A, is reported. d-Glucose 6-phosphate was identified as the substrate for the putative thiosugar biosynthetic protein, BexX, by trapping the covalently bonded enzyme-substrate intermediate. The site-specific modification at K110 residue was determined by mutagenesis studies and LC-MS/MS analysis. A key intermediate carrying a keto functionality was confirmed to exist in the enzyme-substrate complex. These results suggest that the sulfur insertion mechanism in 2-thiosugar biosynthesis shares similarities with that for thiamin biosynthesis.

Original language	English
Pages (from-to)	15544-15546
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	132
Issue number	44
DOIs	https://doi.org/10.1021/ja108061c
Publication status	Published - 2010 Nov 10
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja108061c

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abstract = "The first mechanistic insight into 2-thiosugar production in an angucycline-type antibiotic, BE-7585A, is reported. d-Glucose 6-phosphate was identified as the substrate for the putative thiosugar biosynthetic protein, BexX, by trapping the covalently bonded enzyme-substrate intermediate. The site-specific modification at K110 residue was determined by mutagenesis studies and LC-MS/MS analysis. A key intermediate carrying a keto functionality was confirmed to exist in the enzyme-substrate complex. These results suggest that the sulfur insertion mechanism in 2-thiosugar biosynthesis shares similarities with that for thiamin biosynthesis.",

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Mechanistic studies of the biosynthesis of 2-thiosugar: Evidence for the formation of an enzyme-bound 2-ketohexose intermediate in BexX-catalyzed reaction

Abstract

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