title: Synthesis of fluorinated C-mannopeptides as sialyl Lewisx mimics for E- and P-selectin inhibition.
abstract: The synthesis of fluorinated C-mannopeptides and their evaluation as E- and P-selectin inhibitors is described. These molecules are difluorinated analogues of CH(2)-glycopeptides already reported to act as sLe(x) mimics. The alpha and beta anomers of these CF(2)-glycopeptides have been prepared, as well as their 1-hydroxy analogues which were present in solution as an equilibrium mixture of alpha- and beta-pyranose and alpha- and beta-furanose forms. These molecules showed inhibitory activities comparable to their CH(2) counterparts with a moderate influence of the pseudo-anomeric center configuration.
authors.affiliation: Université et INSA de Rouen, CNRS, UMR6014 & FR3038-IRCOF, Mont Saint-Aignan Cedex, France.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Gouge-Ibert
authors.forename: Camille
authors.initials: C
authors.lastname: Pierry
authors.forename: Florent
authors.initials: F
authors.lastname: Poulain
authors.forename: Anne-Lise
authors.initials: AL
authors.lastname: Serre
authors.forename: Céline
authors.initials: C
authors.lastname: Largeau
authors.forename: Virginie
authors.initials: V
authors.lastname: Escriou
authors.forename: Daniel
authors.initials: D
authors.lastname: Scherman
authors.forename: Philippe
authors.initials: P
authors.lastname: Jubault
authors.forename: Jean-Charles
authors.initials: JC
authors.lastname: Quirion
authors.forename: Eric
authors.initials: E
authors.lastname: Leclerc
mesh_terms: D019040:E-Selectin / Q000187:drug effects*; D005461:Fluorine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D009844:Oligosaccharides / Q000737:chemistry*; D019007:P-Selectin / Q000037:antagonists & inhibitors*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000080506:Sialyl Lewis X Antigen
chemical_list: D019040:E-Selectin; D009844:Oligosaccharides; D019007:P-Selectin; D010455:Peptides; D000080506:Sialyl Lewis X Antigen; D005461:Fluorine