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Synthesis of galactose-mimicking 1H-(1,2,3-triazol-1-yl)-mannosides as selective galectin-3 and 9N inhibitors.

Tejler, Johan LU ; Skogman, Fredrik; Leffler, Hakon LU and Nilsson, Ulf LU (2007) In Carbohydrate Research 342(Mar 14). p.1869-1875
Abstract
1H-[1,2,3]-Triazol-1-yl mannosides have been synthesized as inhibitors for the beta-galactoside-binding family of galectin proteins. Easier synthetic access to C1 in mannose, as compared to C3 in galactose, for attachment of affinity-enhancing triazoles rendered a synthetic advantage. The best mannose-derived inhibitor for galectin-9N, 4-benzylaminocarbonyl-1H-[1,2,3]-triazol-1-yl beta-D-mannopyranoside, had a K-d value of 540 mu M, which compares favorably with its galactoside counterpart (K-d = 670 mu M) and with LacNAc (K-d = 500 mu M). (c) 2007 Elsevier Ltd. All rights reserved.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
glycomimetic, galectin, lectin, mannoside, triazole
in
Carbohydrate Research
volume
342
issue
Mar 14
pages
1869 - 1875
publisher
Elsevier
external identifiers
  • wos:000248745500026
  • scopus:34447315866
ISSN
1873-426X
DOI
10.1016/j.carres.2007.03.012
language
English
LU publication?
yes
id
78b09676-bf40-4db8-8839-704a60ca7447 (old id 167802)
alternative location
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=17407769&dopt=Abstract
date added to LUP
2007-07-04 11:53:29
date last changed
2017-01-01 05:11:55
@article{78b09676-bf40-4db8-8839-704a60ca7447,
  abstract     = {1H-[1,2,3]-Triazol-1-yl mannosides have been synthesized as inhibitors for the beta-galactoside-binding family of galectin proteins. Easier synthetic access to C1 in mannose, as compared to C3 in galactose, for attachment of affinity-enhancing triazoles rendered a synthetic advantage. The best mannose-derived inhibitor for galectin-9N, 4-benzylaminocarbonyl-1H-[1,2,3]-triazol-1-yl beta-D-mannopyranoside, had a K-d value of 540 mu M, which compares favorably with its galactoside counterpart (K-d = 670 mu M) and with LacNAc (K-d = 500 mu M). (c) 2007 Elsevier Ltd. All rights reserved.},
  author       = {Tejler, Johan and Skogman, Fredrik and Leffler, Hakon and Nilsson, Ulf},
  issn         = {1873-426X},
  keyword      = {glycomimetic,galectin,lectin,mannoside,triazole},
  language     = {eng},
  number       = {Mar 14},
  pages        = {1869--1875},
  publisher    = {Elsevier},
  series       = {Carbohydrate Research},
  title        = {Synthesis of galactose-mimicking 1H-(1,2,3-triazol-1-yl)-mannosides as selective galectin-3 and 9N inhibitors.},
  url          = {http://dx.doi.org/10.1016/j.carres.2007.03.012},
  volume       = {342},
  year         = {2007},
}