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Issue 25, 2020
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Comparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents

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Abstract

Late oxidation of hexose based building blocks or the use of uronic acid containing building blocks are two complementary strategies in the synthesis of glycosaminoglycans, the latter simplifiying the later stages of the process. Here we report the synthesis and evaluation of various disaccharide donors—uronic acids and their pyranose equivalents—for the synthesis of heparan sulfate, using an established protective group strategy. Hexose based “imidate” type donors perform well in the studied glycosylations, while their corresponding uronate esters fall short; a uronate ester thioglycoside performs equal to, if not better than, a hexose thioglycoside equivalent.

Graphical abstract: Comparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents

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Supplementary files

Article information


Submitted
31 Mar 2020
Accepted
08 Jun 2020
First published
09 Jun 2020

Org. Biomol. Chem., 2020,18, 4728-4733
Article type
Communication

Comparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents

D. J. Sheppard, S. A. Cameron, P. C. Tyler and R. Schwörer, Org. Biomol. Chem., 2020, 18, 4728
DOI: 10.1039/D0OB00671H

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