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




Modular Synthesis of Heparin-Related Tetra-, Hexa- and Octasaccharides with Differential O-6 Protections: Programming for Regiodefined 6-O-Modifications - Download this document for free, or read online. Document in PDF available to download.

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

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





Author: Marek Baráth 1,†, Steen U. Hansen 1,‡, Charlotte E. Dalton 1,‡, Gordon C. Jayson 2, Gavin J. Miller 1,§ and John M. Gardiner 1,*

Source: http://mdpi.com/



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