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Molecules 2015, 20(4), 6167-6180; doi:10.3390/molecules20046167

Modular Synthesis of Heparin-Related Tetra-, Hexa- and Octasaccharides with Differential O-6 Protections: Programming for Regiodefined 6-O-Modifications

1
Manchester Institute of Biotechnology and the School of Chemistry, 131 Princess Street, The University of Manchester, Manchester M1 7DN, UK
2
Institute of Cancer Sciences, Christie Hospital and University of Manchester, Wilmslow Road, Manchester M20 4BX, UK
Present address: Institute of Chemistry, Centre of Glycomics, Dubravska Cesta 9, Bratislava 845 38, Slovakia.
These authors contributed equally to this work.
§
Present address: School of Chemistry, University of Manchester, Manchester M13 9PL, UK.
*
Author to whom correspondence should be addressed.
Academic Editor: Vito Ferro
Received: 28 December 2014 / Revised: 6 March 2015 / Accepted: 16 March 2015 / Published: 9 April 2015
(This article belongs to the Special Issue Glycosaminoglycans and Their Mimetics)
View Full-Text   |   Download PDF [1057 KB, uploaded 9 April 2015]   |  

Abstract

Heparin and heparan sulphate (H/HS) are important members of the glycosaminoglycan family of sugars that regulate a substantial number of biological processes. Such biological promiscuity is underpinned by hetereogeneity in their molecular structure. The degree of O-sulfation, particularly at the 6-position of constituent D-GlcN units, is believed to play a role in modulating the effects of such sequences. Synthetic chemistry is essential to be able to extend the diversity of HS-like fragments with defined molecular structure, and particularly to deconvolute the biological significance of modifications at O6. Here we report a synthetic approach to a small matrix of protected heparin-type oligosaccharides, containing orthogonal D-GlcN O-6 protecting groups at programmed positions along the chain, facilitating access towards programmed modifications at specific sites, relevant to sulfation or future mimetics. View Full-Text
Keywords: heparin; oligosaccharide; iduronate; GAG mimetic heparin; oligosaccharide; iduronate; GAG mimetic
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Baráth, M.; Hansen, S.U.; Dalton, C.E.; Jayson, G.C.; Miller, G.J.; Gardiner, J.M. Modular Synthesis of Heparin-Related Tetra-, Hexa- and Octasaccharides with Differential O-6 Protections: Programming for Regiodefined 6-O-Modifications. Molecules 2015, 20, 6167-6180.

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