Hansen, SU, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Cliff, MJ, Jaysonc, GC and Gardiner, JM (2015) Making the longest sugars: a chemical synthesis of heparin-related [4](n) oligosaccharides from 16-mer to 40-mer. Chemical Science, 6 (11). 6158 - 6164.

G Miller - Making the longest sugars - a chemical synthesis of heparin-related 4n oligosaccharides from 16-mer to 40-mer.pdf - Published Version
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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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Physical and Geographical Sciences
Related URLs:
Depositing User: Symplectic
Date Deposited: 26 Nov 2015 11:36
Last Modified: 15 May 2019 08:40
URI: https://eprints.keele.ac.uk/id/eprint/1222

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