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Synthesis of fluorinated C-mannopeptides as sialyl Lewisx mimics for E- and P-selectin inhibition. 2010
Vanessa Gouge-Ibert, and
Camille Pierry, and
Florent Poulain, and
Anne-Lise Serre, and
Céline Largeau, and
Virginie Escriou, and
Daniel Scherman, and
Philippe Jubault, and
Jean-Charles Quirion, and
Eric Leclerc
Université et INSA de Rouen, CNRS, UMR6014 & FR3038-IRCOF, Mont Saint-Aignan Cedex, France.
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.
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