417711-01-4Relevant academic research and scientific papers
Exploration of conformational flexibility and hydrogen bonding of xylosides in different solvents, as a model system for enzyme active site interactions
R?nnols, Jerk,Manner, Sophie,Siegbahn, Anna,Ellervik, Ulf,Widmalm, G?ran
, p. 5465 - 5472 (2013/09/02)
The predominantly populated conformation of carbohydrates in solution does not necessarily represent the biologically active species; rather, any conformer accessible without too large an energy penalty may be present in a biological pathway. Thus, the conformational preferences of a naphthyl xyloside, which initiates in vivo synthesis of antiproliferative glycosaminoglycans, have been studied by using NMR spectroscopy in a variety of solvents. Equilibria comprising the conformations 4C1, 2S O and 1C4 were found, with a strong dependence on the hydrogen bonding ability of the solvent. Studies of fluorinated analogues revealed a direct hydrogen bond from the hydroxyl group at C2 to the fluorine atom at C4 by a 1hJF4,HO2 coupling. Hydrogen bond directionality was further established via comparisons of fluorinated levoglucosan molecules. The Royal Society of Chemistry.
Parasite glycoconjugates. Part 12. Synthesis of deoxy, fluorodeoxy and aminodeoxy disaccharide phosphates, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania
Yashunsky, Dmitry V.,Tsvetkov, Yury E.,Ferguson, Michael A.J.,Nikolaev, Andrei V.
, p. 242 - 256 (2007/10/03)
A set of phosphodisaccharides, structural analogues of the β-D-galactosyl-(1→4)-α-D-mannosyl phosphate 1, are synthesized using the Koenigs-Knorr method for the glycosylation reactions and the glycosyl hydrogenphosphonate method for phosphorylation. The c
