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Updated: Oct 9, 2025

Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling
Published on: February 5, 2018
Direct Synthesis of Glycans Containing Challenging ManNAcA Residues
Catherine Alex1, Alexei V Demchenko1,2
1Department of Chemistry and Biochemistry, University of Missouri─St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States.
Abstract:
A method for direct, highly stereoselective synthesis of glycans containing β-linked d-mannosaminuronic acid (ManNAcA) residues is reported herein, among which is the capsular polysaccharide of Staphylococcus aureus type 8. Previous chemical syntheses of this glycan relied on indirect methods comprising glucosylation followed by a multistep epimerization and oxidation sequence. The high β-stereocontrol with direct glycosidation of 3-O-picoloylated ManNAcA donors was achieved using the H-bond-mediated aglycone delivery (HAD) reaction. A method to achieve complete α-ManNAcA stereoselectivity with 3-O-benzoylated donors is also reported.
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