title: The conformational behaviour and P-selectin inhibition of fluorine-containing sialyl LeX glycomimetics.
abstract: A combination of experimental J/NOE NMR data with molecular mechanics and dynamics calculations has been used to examine the conformational behaviour and assign the configuration of synthetically prepared epimeric 3-carboxymethyl-O-Gal-(1-->1)-alpha-Man-fluoro-C-glycosides. It is shown that the population distributions around the glycosidic linkages strongly depend on the configuration at the fluorinated carbon of the pseudoacetal residue. It is also shown that these compounds resemble the inhibition ability of sialyl LeX towards P-selectin.
authors: Centro de Investigaciones Biológicas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain. jjbarbero@cib.csic.es. jpercas@ceu.es
authors: Javier
authors: J
authors: Pérez-Castells
authors: José Juan
authors: JJ
authors: Hernández-Gay
authors: Richard W
authors: RW
authors: Denton
authors: Kurissery A
authors: KA
authors: Tony
authors: David R
authors: DR
authors: Mootoo
authors: Jesús
authors: J
authors: Jiménez-Barbero
mesh_terms: D002236:Carbohydrate Conformation; D003198:Computer Simulation; D006027:Glycosides / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008956:Models, Chemical; D008958:Models, Molecular; D018716:Molecular Mimicry; D009844:Oligosaccharides / Q000737:chemistry*; D019007:P-Selectin / Q000737:chemistry*; D012015:Reference Standards; D012680:Sensitivity and Specificity; D000080506:Sialyl Lewis X Antigen; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013997:Time Factors
chemical_list: D006027:Glycosides; D009844:Oligosaccharides; D019007:P-Selectin; D000080506:Sialyl Lewis X Antigen