Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5226796 | Tetrahedron | 2006 | 9 Pages |
Abstract
Methyl β-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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Anders Bergh, Hakon Leffler, Anders Sundin, Ulf J. Nilsson, Nina Kann,