Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors

Summary, in English

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: Anders Bergh; Hakon Leffler; Anders Sundin; Ulf Nilsson; Nina Kann
• Avdelning/ar: Avdelningen för mikrobiologi, immunologi och glykobiologi - MIG; Centrum för analys och syntes
• Publiceringsår: 2006
• Språk: Engelska
• Sidor: 8309-8317
• Publikation/Tidskrift/Serie: Tetrahedron
• Volym: 62
• Issue: 35
• Länkar: http://dx.doi.org/10.1016/j.tet.2006.06.057
• Dokumenttyp: Artikel i tidskrift
• Förlag: Elsevier
• Ämne: Microbiology in the medical area; Immunology in the medical area
• Status: Published
• ISBN/ISSN/Övrigt: ISSN: 0040-4020