Synthesis of 3-amido-3-deoxy-beta-D-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors

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Abstract

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.

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Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Immunology in the medical area
  • Microbiology in the medical area

Keywords

  • Talose, Talopyranoside, Talosamide, Galectin, Galectin-4C
Original languageEnglish
Pages (from-to)9164-9172
JournalTetrahedron
Volume67
Issue number47
Publication statusPublished - 2011
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Division of Microbiology, Immunology and Glycobiology - MIG (013025200)