Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors
Artikel i vetenskaplig tidskrift, 2006

Methyl beta-D-galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.

Författare

A. Bergh

Chalmers University of Technology

H. Leffler

Lunds universitet

A. Sundin

Lunds universitet

U. J. Nilsson

Lunds universitet

Nina Kann

Chalmers, Kemi- och bioteknik, Organisk kemi

Tetrahedron

0040-4020 (ISSN)

Vol. 62 8309-8317

Ämneskategorier

Kemi

DOI

10.1016/j.tet.2006.06.057