Synthesis of 3-amido-3-deoxy-beta-D-talopyranosides: all-cis-substituted pyranosides as lectin inhibitors
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/2227416
- author
- Öberg, Christopher LU ; Noresson, Ann-Louise LU ; Leffler, Hakon LU and Nilsson, Ulf LU
- organization
- publishing date
- 2011
- 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}}, }