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Issue 11, 2015
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Making the longest sugars: a chemical synthesis of heparin-related [4]n oligosaccharides from 16-mer to 40-mer

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Abstract

The chemical synthesis of long oligosaccharides remains a major challenge. In particular, the synthesis of glycosaminoglycan (GAG) oligosaccharides belonging to the heparin and heparan sulfate (H/HS) family has been a high profile target, particularly with respect to the longer heparanome. Herein we describe a synthesis of the longest heparin-related oligosaccharide to date and concurrently provide an entry to the longest synthetic oligosaccharides of any type yet reported. Specifically, the iterative construction of a series of [4]n-mer heparin-backbone oligosaccharides ranging from 16-mer through to the 40-mer in length is described. This demonstrates for the first time the viability of generating long sequence heparanoids by chemical synthesis, via practical solution-phase synthesis. Pure-Shift HSQC NMR provides a dramatic improvement in anomeric signal resolution, allowing full resolution of all 12 anomeric protons and extrapolation to support anomeric integrity of the longer species. A chemically pure 6-O-desfulfated GlcNS-IdoAS icosasaccharide (20-mer) represents the longest pure synthetic heparin-like oligosaccharide.

Graphical abstract: Making the longest sugars: a chemical synthesis of heparin-related [4]n oligosaccharides from 16-mer to 40-mer

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Supplementary files

Article information


Submitted
04 May 2015
Accepted
23 Jul 2015
First published
24 Jul 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 6158-6164
Article type
Edge Article
Author version available

Making the longest sugars: a chemical synthesis of heparin-related [4]n oligosaccharides from 16-mer to 40-mer

S. U. Hansen, G. J. Miller, M. J. Cliff, G. C. Jayson and J. M. Gardiner, Chem. Sci., 2015, 6, 6158
DOI: 10.1039/C5SC02091C

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