Issue 25, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
31 Mas 2020
Accepted
08 Jun 2020
First published
09 Jun 2020

Org. Biomol. Chem., 2020,18, 4728-4733

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements