Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation

Pauline Peltier-Pain; Karen Marchillo; Maoquan Zhou; David R. Andes; Jon S. Thorson

doi:10.1021/ol3023374

Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation

Pauline Peltier-Pain, Karen Marchillo, Maoquan Zhou, David R. Andes, Jon S. Thorson

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

34 Scopus citations

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.

Original language	English
Pages (from-to)	5086-5089
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	19
DOIs	https://doi.org/10.1021/ol3023374
State	Published - Oct 5 2012

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3023374

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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.",

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AU - Peltier-Pain, Pauline

AU - Marchillo, Karen

AU - Zhou, Maoquan

AU - Andes, David R.

AU - Thorson, Jon S.

PY - 2012/10/5

Y1 - 2012/10/5

N2 - 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.

AB - 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.

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JO - Organic Letters

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Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation

Abstract

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