Marek Baráth
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.
Authors
Steen U. Hansen
Charlotte E. Dalton
Gordon C. Jayson
Gavin Miller g.j.miller@keele.ac.uk
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.
| 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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Modular synthesis of heparin-related tetra-, hexa- and octasaccharides with differential o-6 protections: programming for regiodefined 6-o-modifications..pdf
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Publisher Licence URL
https://creativecommons.org/licenses/by/4.0/
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