Diversity-Oriented Chemoenzymatic Synthesis of Sulfated and Nonsulfated Core 2 <i>O</i>-GalNAc Glycans
Zhuojia Xu, Yaqi Deng, Zhumin Zhang, Wenjing Ma, Wanjin Li, Liuqing Wen, Tiehai Li
Abstract
A diversity-oriented chemoenzymatic approach for the collective preparation of sulfated core 2 O-GalNAc glycans and their nonsulfated counterparts was described. A sulfated trisaccharide and a nonsulfated trisaccharide were chemically synthesized by combining flexible protected group manipulations and sequential one-pot glycosylations. The divergent enzymatic extension of these two trisaccharides, using a panel of robust glycosyltransferases that can recognize sulfated substrates and differentiating the branches with specifically designed glycosylation sequences to achieve regioselective sialylation, provided 36 structurally well-defined O-GalNAc glycans.
Topics & Concepts
TrisaccharideGlycanGlycosylationGlycosyltransferaseSulfationChemistryRegioselectivityEnzymeStereochemistryBiochemistryGlycoproteinCatalysisCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchEnzyme Production and Characterization