title: Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy.
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.
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, UK.
authors.forename: Gavin J
authors.initials: GJ
authors.lastname: Miller
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, UK.
authors.forename: Steen U
authors.initials: SU
authors.lastname: Hansen
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, UK.
authors.forename: Marek
authors.initials: M
authors.lastname: Baráth
authors.affiliation: Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN, UK; Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B2020 Antwerp, Belgium.
authors.forename: Christian
authors.initials: C
authors.lastname: Johannessen
authors.affiliation: Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN, UK.
authors.forename: Ewan W
authors.initials: EW
authors.lastname: Blanch
authors.affiliation: Institute of Cancer Sciences, Christie Hospital and University of Manchester, Wilmslow Road, Manchester M20 4BX, UK.
authors.forename: Gordon C
authors.initials: GC
authors.lastname: Jayson
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, UK. Electronic address: gardiner@manchester.ac.uk.
authors.forename: John M
authors.initials: JM
authors.lastname: Gardiner
mesh_terms: D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry; D006493:Heparin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007067:Iduronic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013059:Spectrum Analysis, Raman; D013431:Sulfates / Q000737:chemistry*
chemical_list: D004187:Disaccharides; D006017:Glycolipids; D013431:Sulfates; C464536:heparin disaccharide; D007067:Iduronic Acid; D006493:Heparin
keywords: Disaccharides; Heparin; Iduronic aid; Raman–ROA; Sulfated carbohydrates