title: Gas-phase and solution conformations of selected dimeric structural units of heparin.
abstract: The molecular structure of four dimeric units (D-E, E-F, F-G, and G-H) of the DEFGH structural unit of heparin, their anionic forms, and their sodium salts have been studied using the B3LYP/6-31+G(d) method. The optimized geometries indicate that the most stable structure of these dimeric units in neutral state is stabilized via "bifurcated" sodium bonds. The equilibrium structure of the biologically active anionic forms of the glycosaminoglycans studied changed considerably in a water solution. The stable-energy conformations around glysosidic bonds found for the individual dimeric species investigated are in agreement with the available experimental structural data for the structurally related heparin-derived oligosaccharides.
authors.affiliation: Department of Pharmaceutical Chemistry, Comenius University, Odbojarov 10, SK-832 32 Bratislava, Slovakia, and German Cancer Research Center, Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany. remko@fpharm.uniba.sk
authors.forename: Milan
authors.initials: M
authors.lastname: Remko
authors.forename: Claus-Wilhelm
authors.initials: CW
authors.lastname: von der Lieth
mesh_terms: D002236:Carbohydrate Conformation; D019281:Dimerization; D005740:Gases; D006027:Glycosides / Q000737:chemistry; D006493:Heparin / Q000737:chemistry*; D008958:Models, Molecular
chemical_list: D005740:Gases; D006027:Glycosides; D006493:Heparin