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Issue 25, 2020
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Synthesis of oligosaccharides of the linkage region of proteoglycans using regioselective glycosylation

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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

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Supplementary files

Article information


Submitted
16 Apr 2020
Accepted
10 Jun 2020
First published
16 Jun 2020

Org. Biomol. Chem., 2020,18, 4831-4842
Article type
Paper

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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