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

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 35 8309-8317

Ämneskategorier

Kemi

DOI

10.1016/j.tet.2006.06.057