Conformational Study of D 4-UronateMonosaccharide and Glycosaminoglycan-derived Disaccharide
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Authors
Bazin, H.G.
Capila, I.
Linhardt, Robert J.
Issue Date
1998
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Alternative Title
Abstract
Sixteen delta 4-uronate monosaccharides were chemically synthesized. Their carboxy group was protected as a methyl or benzyl ester, the anomeric hydroxyl group as a benzyl glycoside and the 2 and 3 hydroxyl groups were protected with different substitution patterns as both ester and ether derivatives. Disaccharides containing delta 4-uronates were prepared from heparin layses. Their carboxy group was unprotected or protected as a benzyl ester and the two hydroxyls in the uronate moiety were free, as O-sulfo derivates or acylated. The conformation of these unsaturated uronate monosaccharide and disaccharide residues was studied using 1H NMR by examining interproton vicinal coupling constants. The delta 4-uronate residue adopted either the 2H1 or the 1H2 conformations. The equilibrium between these two conformers was shown to be controlled by substitution pattern.
Description
Carbohydrate Research, 309,135-144
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Full Citation
Conformational Study of D 4-UronateMonosaccharide and Glycosaminoglycan-derived Disaccharide, H.G. Bazin,I. Capila, R.J. Linhardt, Carbohydrate Research, 309,135-144, 1998.