Synthesis of O-galactosyl Aldoximes As Potent LacNAc-mimetic Galectin-3 Inhibitors

Overview

Journal Bioorg Med Chem Lett

Specialty Biochemistry

Date 2005 Apr 20

PMID 15837322

Citations 14

Authors

Johan Tejler

Hakon Leffler

Ulf J Nilsson

Affiliations

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Abstract

A panel of anomeric oxime ether derivatives of beta-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 Kd value of 180 microM, which is 24 times better than methyl beta-D-galactopyranoside (Kd=4400 microM) and in the same range as methyl lactoside (Kd=220 microM).

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