Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/388776
- author
- Bergh, Anders ; Leffler, Hakon LU ; Sundin, Anders LU ; Nilsson, Ulf LU and Kann, Nina
- organization
- publishing date
- 2006
- 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
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)
- id
- 803d69ee-d683-43e5-b871-b57be4da03f4 (old id 388776)
- date added to LUP
- 2016-04-01 15:38:01
- date last changed
- 2022-01-28 06:16:37
@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}}, doi = {{10.1016/j.tet.2006.06.057}}, volume = {{62}}, year = {{2006}}, }