775265-12-8

Upstream product

• 187402-17-1 benzyl (2S)-3-azido-2-O-{1-O-[(1R,2R)-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)cyclohexyl]-6-O-benzyl-β-D-galactopyranos-3-yl}propionate 

Downstream Products

• 1210975-36-2 (2S)-3-azido-2-O-{1-O-[(1R,2R)-2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}propanoic acid 

Relevant academic research and scientific papers

Probing the carbohydrate recognition domain of E-selectin: The importance of the acid orientation in sLex mimetics

The selectin-leukocyte interaction is the initial event in the early inflammatory cascade. This interplay proceeds via the terminal tetrasaccharide sialyl Lewisx (sLex), present on physiological selectin ligands and E- and P-selectins located on the endothelial surface. Blocking this process is regarded as a promising therapeutic approach for inflammatory diseases where excessive leukocyte efflux is responsible for tissue damage. Selectin antagonists are generally based on sLex as lead structure, containing the essential pharmacophores pre-oriented in the bioactive conformation. In this work, we describe a set of competitive sLex mimetics possessing the carboxylic acid pharmacophore equipped with additional hydrophobic substituents as neuraminic acid (Neu5Ac) replacements. This small library of antagonists derived from Huisgen-1,3-dipolar cycloadditions allows to further probe the carbohydrate recognition domain of E-selectin.