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

Baráth, Marek; Hansen, Steen U.; Dalton, Charlotte E.; Jayson, Gordon C.; Miller, Gavin J.; Gardiner, John M.

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


Authors

Marek Baráth

Steen U. Hansen

Charlotte E. Dalton

Gordon C. Jayson

John M. Gardiner



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.

Citation

Baráth, M., Hansen, S. U., Dalton, C. E., Jayson, G. C., Miller, G. J., & Gardiner, J. M. (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. https://doi.org/10.3390/molecules20046167

Journal Article Type Article
Acceptance Date Mar 16, 2015
Online Publication Date Apr 9, 2015
Publication Date Apr 9, 2015
Publicly Available Date May 26, 2023
Journal Molecules
Publisher MDPI
Peer Reviewed Peer Reviewed
Volume 20
Issue 4
Pages 6167 - 6180
DOI https://doi.org/10.3390/molecules20046167
Keywords heparin, oligosaccharide, iduronate, GAG mimetic
Publisher URL http://www.mdpi.com/1420-3049/20/4/6167

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