structure of sulfated monosaccharides studied by quantum chemical methods硫酸单糖结构研究了量子化学方法.pdf

Molecules 2003, 8, 770-779 molecules ISSN 1420-3049 Structure of Sulfated Monosaccharides Studied by Quantum Chemical Methods. Eva Scholtzová 1,*, Pavel Mach 1 and Miloš Hricovíni 2 1 Institute of Inorganic Chemistry of Slovak Academy of Sciences, D˙bravsk· cesta 9, Bratislava, Slovak Republic, SK-845 36. Tel. (2)59410-457, Fax (2)59410-444. 2 Chemical Institute of Slovak Academy of Sciences, D˙bravsk· cesta 9, Bratislava, Slovak Republic, SK-845 36. * Author to whom correspondence should be addressed; e-mail: uacheva@savba.sk Received: 21 May 2003; in revised form: 15 October 2003 / Accepted: 20 October 2003 / Published: 15 November 2003 Abstract: Ab initio and DFT analysis have been used to study of geometry of sulfated monosaccharides GlcN,6-SO3- and IdoA 2-SO3- in solvent. The computed low conformational barrier between the interconverting conformers of the IdoA 2-SO3- residue is in agreement with experimental data. Keywords: Sulfated monosaccharides; structure; ab initio; DFT; solvent. Introduction Modeling of biologically active saccharides aims to understand the molecular details of their biological functions. Sulfated saccharides, owing to their structural peculiarities, are among those saccharide derivatives that are most difficult to model. These difficulties are due to the presence of numerous negatively charged sulfate groups that vary in position in oligo- and polysaccharide chains and that influence the conformation of the monosaccharide units and the glycosidic linkages. Heparin is probably the best known sulfated sacc