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Issue 14, 2020
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S-Glycosides: synthesis of S-linked arabinoxylan oligosaccharides

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Abstract

S-Glycosides are important tools for the elucidation of specific protein–carbohydrate interactions and can significantly aid structural and functional studies of carbohydrate-active enzymes, as they are often inert or act as enzyme inhibitors. In this context, this work focuses on the introduction of an S-linkage into arabinoxylan oligosaccharides (AXs) in order to obtain a small collection of synthetic tools for the study of AXs degrading enzymes. The key step for the introduction of the S-glycosidic linkage involved anomeric thiol S-alkylation of an orthogonally protected L-arabinopyranoside triflate. The resulting S-linked disaccharide was subsequently employed in a series of glycosylation reactions to obtain a selectively protected tetrasaccharide. This could be further elaborated through chemoselective deprotection and glycosylation reactions to introduce branching L-arabinofuranosides.

Graphical abstract: S-Glycosides: synthesis of S-linked arabinoxylan oligosaccharides

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Supplementary files

Article information


Submitted
04 Mar 2020
Accepted
17 Mar 2020
First published
17 Mar 2020

Org. Biomol. Chem., 2020,18, 2696-2701
Article type
Paper

S-Glycosides: synthesis of S-linked arabinoxylan oligosaccharides

C. Romanò, H. Jiang, I. Boos and M. H. Clausen, Org. Biomol. Chem., 2020, 18, 2696
DOI: 10.1039/D0OB00470G

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