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Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors

Bergh, Anders; Leffler, Hakon LU ; Sundin, Anders LU ; Nilsson, Ulf LU and Kann, Nina (2006) In Tetrahedron 62(35). p.8309-8317
Abstract
Methyl beta-D-galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron
volume
62
issue
35
pages
8309 - 8317
publisher
Elsevier
external identifiers
  • wos:000239885200008
  • scopus:33745967791
ISSN
0040-4020
DOI
10.1016/j.tet.2006.06.057
language
English
LU publication?
yes
id
803d69ee-d683-43e5-b871-b57be4da03f4 (old id 388776)
date added to LUP
2007-09-28 09:56:11
date last changed
2019-01-06 09:47:59
@article{803d69ee-d683-43e5-b871-b57be4da03f4,
  abstract     = {Methyl beta-D-galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.},
  author       = {Bergh, Anders and Leffler, Hakon and Sundin, Anders and Nilsson, Ulf and Kann, Nina},
  issn         = {0040-4020},
  language     = {eng},
  number       = {35},
  pages        = {8309--8317},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors},
  url          = {http://dx.doi.org/10.1016/j.tet.2006.06.057},
  volume       = {62},
  year         = {2006},
}