CONFORMATION of the UNSATURATED URONIC-ACID RESIDUES of GLYCOSAMINOGLYCAN DISACCHARIDES

CONFORMATION of the UNSATURATED URONIC-ACID RESIDUES of GLYCOSAMINOGLYCAN DISACCHARIDES

Autor Ragazzi, M. Google Scholar
Ferro, D. R. Google Scholar
Provasoli, A. Google Scholar
Pumilia, P. Google Scholar
Cassinari, A. Google Scholar
Torri, G. Google Scholar
Guerrini, M. Google Scholar
Casu, B. Google Scholar
Nader, H. B. Google Scholar
Dietrich, C. P. Google Scholar
Instituição IST CHIM & BIOCHIM G RONZONI
Universidade Federal de São Paulo (UNIFESP)
Resumo Molecular mechanics calculations (using the REFINE package) have been performed on a series of disaccharides obtained by cleavage of glycosaminoglycans with lyases, in order to examine the effect of chemical environment on the conformation of the 4,5-unsaturated uronic acid residue. the disaccharides were derived from heparin and heparan sulfate (1-5), hyaluronic acid (6), chondroitin (7), chondroitin-4-sulfate (8), and chondroitin-6-sulfate (9). the H-1 NMR spectra were analysed for the above compounds and for the unsaturated uronic acid residues of a low-molecular weight E. Coli K5 polysaccharide (10), as well as for the alditol derivative (11) of compound 8; the wide variation of the interproton vicinal coupling constants as a function of configuration and position of the glycosidic linkages and of the sulfation pattern is unequivocally interpreted in terms of equilibrium between two distinct ring forms, namely H-2(1) and H-1(2). the equilibrium is semi-quantitatively explained by the results of the present energy calculations.
Idioma Inglês
Data de publicação 1993-01-01
Publicado em Journal of Carbohydrate Chemistry. New York: Marcel Dekker Inc, v. 12, n. 4-5, p. 523-535, 1993.
ISSN 0732-8303 (Sherpa/Romeo, fator de impacto)
Publicador Marcel Dekker Inc
Extensão 523-535
Fonte http://dx.doi.org/10.1080/07328309308019405
Direito de acesso Acesso restrito
Tipo Artigo
Web of Science WOS:A1993LL81800011
Endereço permanente http://repositorio.unifesp.br/handle/11600/25298

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