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Updated: Jun 26, 2026

Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling
Published on: February 5, 2018
Carbasugar-thioether pseudodisaccharides related to N-glycan biosynthesis
Ian Cumpstey1, Dominic S Alonzi, Terry D Butters
1Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, Stockholm, Sweden. cumpstey@organ.su.se
Abstract:
Analogues of the alpha-Glcp-(1-->3)-alpha-Glcp and alpha-Glcp-(1-->3)-alpha-Manp disaccharides (representing the two alpha-gluco linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis) in which the non-reducing-end sugar is replaced by a carbasugar and the inter-glycosidic oxygen by a sulfur were synthesised. The key coupling step was an S(N)2 displacement of an equatorial triflate at C-1 of the carbasugar by C-3 gluco or manno thiolates with inversion of configuration to give thioether pseudodisaccharides with axial substitution at C-1 of the carbasugar. The deprotected pseudodisaccharides failed to inhibit the action of alpha-Glucosidase II as measured both by an in vitro assay and by free oligosaccharide (FOS) analysis from cell studies.
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