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

Öberg, Christopher LU ; Noresson, Ann-Louise LU ; Leffler, Hakon LU and Nilsson, Ulf LU (2011) In Tetrahedron 67(47). p.9164-9172
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... (More)
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. (Less)
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Talose, Talopyranoside, Talosamide, Galectin, Galectin-4C
in
Tetrahedron
volume
67
issue
47
pages
9164 - 9172
publisher
Elsevier
external identifiers
  • wos:000296988800016
  • scopus:80054749114
ISSN
0040-4020
DOI
10.1016/j.tet.2011.09.098
language
English
LU publication?
yes
additional info
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)
id
79a5ed68-94c2-4df3-a51a-acfea0482c7a (old id 2227416)
date added to LUP
2016-04-01 14:09:24
date last changed
2022-01-27 23:01:24
@article{79a5ed68-94c2-4df3-a51a-acfea0482c7a,
  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.}},
  author       = {{Öberg, Christopher and Noresson, Ann-Louise and Leffler, Hakon and Nilsson, Ulf}},
  issn         = {{0040-4020}},
  keywords     = {{Talose; Talopyranoside; Talosamide; Galectin; Galectin-4C}},
  language     = {{eng}},
  number       = {{47}},
  pages        = {{9164--9172}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron}},
  title        = {{Synthesis of 3-amido-3-deoxy-beta-D-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors}},
  url          = {{http://dx.doi.org/10.1016/j.tet.2011.09.098}},
  doi          = {{10.1016/j.tet.2011.09.098}},
  volume       = {{67}},
  year         = {{2011}},
}