Characterisation of oligosaccharides from the chondroitin/dermatan sulphates: (1)H and (13)C NMR studies of oligosaccharides generated by nitrous acid depolymerisation

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 NaBH(4) and purified by ion exchange chromatography. Whereas enzymatic depolymerisation leads...

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Bibliographic Details
Published in:Carbohydrate research 2011-10, Vol.346 (14), p.2222-2227
Main Authors: Lauder, Robert M, Huckerby, Thomas N, Nieduszynski, Ian A, Sadler, Ian H
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Chondroitin - chemistry
Dermatan Sulfate - chemistry
Glucuronic Acid - chemistry
Iduronic Acid - chemistry
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Nitrous Acid - chemistry
Oligosaccharides - chemistry
Polymerization
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Summary: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 NaBH(4) 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 (1)H and (13)C 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.
ISSN:1873-426X
DOI:10.1016/j.carres.2011.06.033