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Open AccessArticle

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
*
Author to whom correspondence should be addressed.
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.
Academic Editor: Vito Ferro
Molecules 2015, 20(4), 6167-6180; https://doi.org/10.3390/molecules20046167
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)
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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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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