Chemoenzymatic synthesis and lectin array characterization of a class of N-glycan clusters.

Journal of the American Chemical Society
Wei HuangLai-Xi Wang

Abstract

N-Glycans are major components of many glycoproteins. These sugar moieties are frequently involved in important physiological and disease processes via their interactions with a variety of glycan-binding proteins (GBP). Clustering effect is an important feature in many glycan-lectin interactions. We describe in this paper a chemoenzymatic synthesis of novel N-glycan clusters using a tandem endoglycosidase-catalyzed transglycosylation. It was found that the internal beta-1,2-linked GlcNAc moieties in the N-glycan core, once exposed in the nonreducing terminus, was able to serve as acceptors for transglycosylation catalyzed by Endo-A and EndoM-N175A. This efficient chemoenzymatic method allows a quick extension of the sugar chains to form a class of glycan clusters in which sugar residues are all connected by native glycosidic linkages found in natural N-glycans. In addition, a discriminative enzymatic reaction at the two GlcNAc residues could be fulfilled to afford novel hybrid clusters. Lectin microarray studies revealed unusual properties in glyco-epitope expression by this panel of structurally well-defined synthetic N-glycans. These new compounds are likely valuable for functional glycomics studies to unveil new functions of...Continue Reading

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Citations

Dec 7, 2011·ACS Chemical Biology·Lai-Xi Wang, Joseph V Lomino
May 14, 2016·ACS Chemical Biology·Phillip M Danby, Stephen G Withers
Dec 10, 2015·Organic & Biomolecular Chemistry·Jian-Song SunJin-Xi Liao
May 6, 2011·Electrophoresis·Jun HirabayashiHiroaki Tateno
Feb 28, 2013·Chemical Society Reviews·Jun HirabayashiHiroaki Tateno
Jan 1, 2011·Trends in Glycoscience and Glycotechnology : TIGG·Lai-Xi Wang
Oct 19, 2017·Organic & Biomolecular Chemistry·Zhigang WuPeng George Wang
Feb 7, 2020·Glycoconjugate Journal·Meifang YangZhongfu Wang
Feb 12, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mei LuoFujiang Guo
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Asuka ShirakawaKoichi Fukase
Aug 25, 2018·Chemical Reviews·Chao Li, Lai-Xi Wang
Jun 29, 2018·Chemical Reviews·Matteo PanzaAlexei V Demchenko
May 9, 2019·The Journal of Organic Chemistry·Salvatore G PistorioAlexei V Demchenko
Sep 15, 2021·Angewandte Chemie·Asuka ShirakawaKoichi Fukase

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