Université et INSA de Rouen, CNRS, UMR6014 & FR3038-IRCOF, Mont Saint-Aignan Cedex, France.
Bioorg Med Chem Lett. 2010 Mar 15;20(6):1957-60. doi: 10.1016/j.bmcl.2010.01.141. Epub 2010 Feb 2.
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.
本文描述了氟化 C-甘露糖肽的合成及其作为 E-和 P-选择素抑制剂的评价。这些分子是已经报道的作为 sLe(x)模拟物的 CH(2)-糖肽的二氟化类似物。这些 CF(2)-糖肽的α和β差向异构体以及它们的 1-羟基类似物已被制备，并且它们在溶液中以α和β吡喃糖和α和β呋喃糖形式的平衡混合物存在。这些分子表现出与它们的 CH(2)对应物相当的抑制活性，伪端基中心构型的影响适中。
