Sialyl Lewisx analogs based on a quinic acid scaffold as the fucose mimic

(−)-Quinic acid was used as a starting material for the preparation of sialyl Lewisx mimetics in order to target E-selectin. Spatial orientation of the hydroxyl groups of quinic acid could mimic the l-fucose ones. Introduction of a side chain ending with a carboxylic acid was effected to replace the sialic acid interaction at the carbohydrate recognition domain. A first series of derivatives, incorporating amino acids linked to quinic acid, were tested for their affinity and found to interact with E-selectin with IC50 within the millimolar range.

Graphical abstract(−)-Quinic acid was used as a starting material for the preparation of sialyl Lewisx mimetics to target E-selectin. Spatial orientation of the hydroxyl groups of quinic acid could mimic the l-fucose ones. Introduction of a side chain ending with a carboxylic acid was effected to replace the sialic acid interaction at the carbohydrate recognition domain. A first series of derivatives, incorporating amino acids linked to quinic acid, were tested for their affinity and found to interact with E-selectin with IC50 within the millimolar range.Figure optionsDownload full-size imageDownload as PowerPoint slide