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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
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
id
79a5ed68-94c2-4df3-a51a-acfea0482c7a (old id 2227416)
date added to LUP
2011-12-23 12:22:17
date last changed
2017-01-01 06:05:23
@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},
  keyword      = {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},
  volume       = {67},
  year         = {2011},
}