Characterisation of oligosaccharides from the chondroitin/dermatan sulphates: H and C NMR studies of oligosaccharides generated by nitrous acid depolymerisation |
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| Authors: | Robert M. Lauder Thomas N. Huckerby Ian A. Nieduszynski Ian H. Sadler |
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| Affiliation: | aFaculty of Health and Medicine, Division of Biomedical and Life Sciences, Lancaster University, Bailrigg, Lancaster LA1 4YQ, UK;bDepartment of Chemistry, The University of Edinburgh, King’s Buildings, West Mains Road, Edinburgh, UK |
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| Abstract: | The polymers chondroitin sulphate and dermatan sulphate have been fragmented by an anhydrous hydrazine/nitrous acid procedure. The resulting disaccharides from the polymer repeat sequences were reduced with NaBH4 and purified by ion exchange chromatography. Whereas enzymatic depolymerisation leads to the loss of the distinction between glucuronic and iduronic acids of CS and DS in the resultant disaccharides, nitrous acid depolymerisation retains these structures. Complete 1H and 13C NMR data have been derived for the major components which were shown to have the structures: GlcA-(β1→3)-anTal6S-ol (I) and l-IdoA-(α1→3)-anTal4S-ol (II), where anTal-ol represents (2,5)anhydro-d-talitol and 6S/4S represent O-ester sulphate groups at C-6/C-4 sites. |
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| Keywords: | Abbreviations: GlcA, font-variant: small-caps" >d-glucuronic acid GlcA-ol, font-variant: small-caps" >d-glucuronic acid alditol IdoA, α- font-variant: small-caps" >l-iduronic acid 6S/4S, O-ester sulphate group on C6/C4 1D, one-dimensional 2D, two-dimensional ΔUA, 4,5-unsaturated hexuronic acid (4-deoxy-α- font-variant: small-caps" >l-threo-hex-4-enepyranosyluronic acid) (2,5)anTal(-ol), (2,5)anhydro- font-variant: small-caps" >d-talose (-talitol) GalNAc(-ol), 2-deoxy-2-N-acetylamino- font-variant: small-caps" >d-galactose (-galactitol) CS, chondroitin sulphate DS, dermatan sulphate GAG, Glycosaminoglycan |
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