1210975-36-2

Upstream product

• 775265-12-8 (2S)-3-amino-2-O-{1-O-[(1R,2R)-2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}propanoic acid 

Downstream Products

• 1210975-43-1 (2S)-3-N-[4-(thiophen-3-yl)-1,2,3-triazol-1-yl]-2-O-{1-O-[(1R,2R)-2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}propionic acid 
• 1210975-45-3 (2S)-3-N-[4-(3-pyridyl)-1,2,3-triazol-1-yl]-2-O-{1-O-[(1R,2R)-2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}propionic acid 
• 1210975-40-8 (2S)-3-N-[4-benzyl-1,2,3-triazol-1-yl]-2-O-{1-O-[(1R,2R)-2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}propionic acid 
• 1210975-46-4 (2S)-3-N-[4-(3-trifluoromethylphenyl)-1,2,3-triazol-1-yl]-2-O-{1-O-[(1R,2R)-2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}propionic acid 
• 1210975-47-5 (2S)-3-N-[4-((1H-benzotriazol-1-yl)methyl)-1,2,3-triazol-1-yl]-2-O-{1-O-[(1R,2R)-2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}propionic 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.