115969-51-2Relevant articles and documents
Synthesis and biological evaluation of a new sialyl Lewis X mimetic derived from lactose
Chervin, Stephanie M.,Lowe, John B.,Koreeda, Masato
, p. 5654 - 5662 (2002)
A sialyl Lewis X (sLex) mimetic compound, 2-(trimethylsilyl)ethyl 3-O-carboxymethyl-β-D-galactopyranosyl-(1→4)-[α-L-fucosyl- (1→6)]-β-D-glucopyranoside (2a), has been synthesized in 14 steps from D-lactose. This synthesis features the use of the activated glycosylating donor, lactosyl iodide, in a Koenigs-Knorr sequence, the regioselective derivatization at the C-3 position of the galactose moiety, and the stereoselective construction of a fucose-α(1→6)-lactose linkage. The mimetic was tested for its ability to inhibit human polymorphonuclear leukocyte (hPMNL) adhesion to immobilized recombinant human E-selectin under shear stress conditions.