Synthesis of O-galactosyl aldoximes as potent LacNAc-mimetic galectin-3 inhibitors

A panel of anomeric oxime ether derivatives of P-galactose were synthesized via the reaction Of O-beta-D-galactopyranosylhydroxylamine with aldehydes. The oxime ethers were evaluated as inhibitors against galectin-3 in a competitive fluorescence polarization assay. The best inhibitor, [E]-O-(beta-D-galactopyranosyl)-indole-3-carbaldoxime (E-52), had a K-d value of 180 mu M, which is 24 times better than methyl beta-D-galactopyranoside (K-d = 4400 mu M) and in the same range as methyl lactoside (K-d = 220 mu M). (c) 2005 Elsevier Ltd. All rights reserved.