Synthesis of 3-amido-3-deoxy-beta-D-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors
Author
Summary, in English
3-Deoxy-3-amino-beta-D-talopyranosides have been synthesized for the first time. The amines were obtained from galactopyranosides through 2,3-anhydrogulosides that were opened to idosides followed by an oxidation/reductive amination sequence. From the amines, 11 corresponding 3-deoxy-3-arylamido-beta-talopyranosides have been synthesized and evaluated as inhibitors against galectin-1, -2, -3, -4C, -4N, -7, -8N and -9N. The synthesized talosamides showed selectivity for Galectin-4C with three of the mono-saccharides having dissociation constants at around 100 mu M against the lectin, which is more than two orders of magnitude better than methyl beta-galactoside and significantly better than the previous best galectin-4C monosaccharide inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.
Department/s
Publishing year
2011
Language
English
Pages
9164-9172
Publication/Series
Tetrahedron
Volume
67
Issue
47
Document type
Journal article
Publisher
Elsevier
Topic
- Immunology in the medical area
- Microbiology in the medical area
Keywords
- Talose
- Talopyranoside
- Talosamide
- Galectin
- Galectin-4C
Status
Published
ISBN/ISSN/Other
- ISSN: 0040-4020