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Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions.

ABSTRACT: We report that simple glycoside donors can drastically shift the equilibria of glycosyltransferase-catalyzed reactions, transforming NDP-sugar formation from an endothermic to an exothermic process. To demonstrate the utility of this thermodynamic adaptability, we highlight the glycosyltransferase-catalyzed synthesis of 22 sugar nucleotides from simple aromatic sugar donors, as well as the corresponding in situ formation of sugar nucleotides as a driving force in the context of glycosyltransferase-catalyzed reactions for small-molecule glycodiversification. These simple aromatic donors also enabled a general colorimetric assay for glycosyltransfer, applicable to drug discovery, protein engineering and other fundamental sugar nucleotide-dependent investigations. This study directly challenges the general notion that NDP-sugars are 'high-energy' sugar donors when taken out of their traditional biological context.

SUBMITTER: Gantt RW

PROVIDER: S-EPMC3177962 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions.

Gantt Richard W RW Peltier-Pain Pauline P Cournoyer William J WJ Thorson Jon S JS

Nature chemical biology 20110821 10

We report that simple glycoside donors can drastically shift the equilibria of glycosyltransferase-catalyzed reactions, transforming NDP-sugar formation from an endothermic to an exothermic process. To demonstrate the utility of this thermodynamic adaptability, we highlight the glycosyltransferase-catalyzed synthesis of 22 sugar nucleotides from simple aromatic sugar donors, as well as the corresponding in situ formation of sugar nucleotides as a driving force in the context of glycosyltransfera ...[more]

PMID: 21857660

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