Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 15, Issue -, Pages 1046-1060Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.15.102
Keywords
C-galactoside; galectin-1; hydroboration; inhibition; selective; triazole
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Funding
- Swedish Research Council [621-2012-2978, 621-2016-03667]
- Royal Physiographic Society, Lund, Sweden
- Knut and Alice Wallenberg Foundation [KAW 2013.0022]
- Galecto Biotech AB, Sweden
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Galectins are carbohydrate recognition proteins that bind carbohydrates containing galactose and are involved in cell signaling and cellular interactions, involving them in several diseases. We present the synthesis of (aryltriazolyl) methyl galactopyranoside galectin inhibitors using a highly diastereoselective hydroboration of C1-exo-methylene pyranosides giving inhibitors with fourfold or better selectivity for galectin-1 over galectin-3, -4C (C-terminal CRD), -4N (N-terminal CRD), -7, -8C, -8N, -9C, and -9N and dissociation constants down to 170 mu M.
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