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Barath, M, Hansen, SU, Dalton, CE, Jayson, GC, Miller, GJ and Gardiner, JM (2015) Modular Synthesis of Heparin-Related Tetra-, Hexa- and Octasaccharides with Differential O-6 Protections: Programming for Regiodefined 6-O-Modifications. Molecules, 20 (4). 6167 - 6180. ISSN 1420-3049
Modular synthesis of heparin-related tetra-, hexa- and octasaccharides with differential o-6 protections: programming for regiodefined 6-o-modifications..pdf - Published Version
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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.
Item Type: | Article |
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Uncontrolled Keywords: | heparin, oligosaccharide, iduronate, GAG mimetic |
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 10:57 |
Last Modified: | 03 May 2019 10:24 |
URI: | https://eprints.keele.ac.uk/id/eprint/1223 |