Glycosidic Linkages

December 5, 2014
Form glycosidic linkages

Abstract Image† Department of Chemical Technology of Drugs, Poznan University of healthcare Sciences, Grunwaldzka 6, 60-780 Poznan, Poland

‡ Institute of Bioorganic Chemistry, Polish Academy of Sciences, Z. Noskowskiego 12/14, 61-704 Poznan, Poland

§ Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland

Cryst. Growth Diverses., 2014, 14 (11), pp 5871–5880

DOI: 10.1021/cg5010962

Synopsis

As shown by thickness practical theory computations, the major factor in charge of the twisted conformation for the disaccharide product of glycyrrhizic acid with its basic and ionic kinds is the tendency associated with COOH/COO¯ categories of the diglucuronic dimer become bridged by a string consists of water molecules and/or cations.

Abstract

Three-dimensional framework of glycyrrhizic acid is dependent upon the conformation regarding the disaccharide unit and its general direction to a virtually rigid aglycone. X-ray crystallography, NMR spectroscopy, and thickness practical concept (DFT) computations were used to analyze the conformational choices associated with glycosidic linkages in solid-state, option and vacuo, respectively. Experimental data have revealed that conformation of glycosidic bonds, which adopted inside solid state, is also favored in answer. The molecular geometry optimizations have shown that a strongly twisted direction for the two glucopyranose units, feature of the solid-state, is stabilized by the bridging communication of water molecules and/or cations with disaccharide COOH/COO¯ groups. Our results illustrate the effect of environment from the favored conformation of disaccharide device into the studied glycoside and point to a potential cause for the noticed rigid conformation associated with the glycosidic bonds in option plus in the solid-state.

Source: pubs.acs.org
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