Issue 25, 2020

Synthesis of oligosaccharides of the linkage region of proteoglycans using regioselective glycosylation

Abstract

Proteoglycans (PGs) are complex macromolecules that are composed of glycosaminoglycan (GAG) chains covalently attached to a core protein through a tetrasaccharide linker. Biosynthesis of PGs is complex and involves a large number of glycosyltranferases. We report herein for the first time the synthesis of a collection of various sulfoforms of the disaccharide GlcA-1,3-β-D-Gal and trisaccharides GlcNAc-1,4-α-D-GlcA-1,3-β-D-Gal and GalNAc-1,4-β-D-GlcA-1,3-β-D-Gal using a regioselective glycosylation. Preliminary results on the impact of sulfation of these disaccharides upon recombinant chondroitin sulfate N-acetylgalactosaminyltransferase-1 (CSGalNAcT-1) involved in chondroitin sulfate chain initiation is also reported.

Graphical abstract: Synthesis of oligosaccharides of the linkage region of proteoglycans using regioselective glycosylation

Supplementary files

Article information

Article type
Paper
Submitted
16 Apr. 2020
Accepted
10 Jūn. 2020
First published
16 Jūn. 2020

Org. Biomol. Chem., 2020,18, 4831-4842

Synthesis of oligosaccharides of the linkage region of proteoglycans using regioselective glycosylation

H. Ledru, B. Ayela, S. Fournel-Gigleux, S. Gulberti and C. Lopin-Bon, Org. Biomol. Chem., 2020, 18, 4831 DOI: 10.1039/D0OB00783H

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