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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.
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author
; ; and
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
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
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
2016-04-01 12:30:05
date last changed
2022-01-27 05:54:19
@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}},
  keywords     = {{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}},
  doi          = {{10.1016/j.carres.2007.03.012}},
  volume       = {{342}},
  year         = {{2007}},
}