1438395-04-0Relevant articles and documents
Monosaccharidic mimetics of the sialyl LewisX tetrasaccharide based on 2,7-dihydroxynaphthalene
Weck, Stefan,Frank, Martin,Hamann, Alf,Opatz, Till
, p. 134 - 148 (2013/09/24)
A potential monosaccharidic mimetic of the sialyl LewisX tetrasaccharide (sLeX) was identified based on an in silico docking study using the crystal structure of an E-selectin-sLeX complex. The chemical synthesis of the mimetic in an ortho-selective C-glycosylation is described. This compound and two close analogues were evaluated in a cell-based selectin binding assay where none of the tested mimetics showed an IC 50 below 1mM. This result can be explained by an unexpected 1C4 conformation of the mannosyl residue which precludes the required binding of the Ca2+-ion in E-selectin.