Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy

Miller, Gavin J.; Hansen, Steen U.; Baráth, Marek; Johannessen, Christian; Blanch, Ewan W.; Jayson, Gordon C.; Gardiner, John M.

doi:10.1016/j.carres.2014.06.026

Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy

Miller, Gavin J.; Hansen, Steen U.; Baráth, Marek; Johannessen, Christian; Blanch, Ewan W.; Jayson, Gordon C.; Gardiner, John M.

Authors

Gavin Miller g.j.miller@keele.ac.uk

Steen U. Hansen

Marek Baráth

Christian Johannessen

Ewan W. Blanch

Gordon C. Jayson

John M. Gardiner

Abstract

Synthesis of an array of differentially sulfated GlcN–IdoA disaccharides, accessible on good scale, directly from l-iduronate components is described. These are specifically directed to provide the sulfation variability at the key most common biologically relevant sulfation-variable l-IdoA O-2 and d-GlcN O-6 and amino sites of this heparin disaccharide. This sulfation-varied matrix has allowed the first evaluation of using Raman/ROA spectroscopy to characterize changes in spectra as a function of both site and level of sulfation with pure, defined heparin-related disaccharide species. This provides analysis of both similarities and differences to digest native heparin and this shows evidence of different types of changes in conformations and conformational freedom as a function of some specific sulfation changes at the disaccharide level. It is anticipated that this data set will open the way for applications to further site-specific sulfated saccharides and demonstrates the capability offered by Raman–ROA towards fingerprinting sulfation in heparin fragments.

Citation

Miller, G. J., Hansen, S. U., Baráth, M., Johannessen, C., Blanch, E. W., Jayson, G. C., & Gardiner, J. M. (2014). Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy. Carbohydrate Research, 400, 44 -53. https://doi.org/10.1016/j.carres.2014.06.026

Journal Article Type	Article
Acceptance Date	Jun 22, 2014
Online Publication Date	Jul 14, 2014
Publication Date	Dec 5, 2014
Journal	Carbohydrate Research
Print ISSN	0008-6215
Publisher	Elsevier
Peer Reviewed	Peer Reviewed
Volume	400
Pages	44 -53
DOI	https://doi.org/10.1016/j.carres.2014.06.026
Keywords	Disaccharides, Heparin, Sulfated carbohydrates, Raman–ROA; Iduronic aid
Publisher URL	http://dx.doi.org/10.1016/j.carres.2014.06.026