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Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation.

ABSTRACT: A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.

SUBMITTER: Peltier-Pain P

PROVIDER: S-EPMC3489467 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation.

Peltier-Pain Pauline P Marchillo Karen K Zhou Maoquan M Andes David R DR Thorson Jon S JS

Organic letters 20120917 19

A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, th ...[more]

PMID: 22984807

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