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Arene-anion based arginine-binding motif on a galactose scaffold : Structure-activity relationships of interactions with arginine-rich galectins

Öberg, Christopher T. LU ; Noresson, Ann Louise LU ; Leffler, Hakon LU and Nilsson, Ulf J. LU (2011) In Chemistry: A European Journal 17(29). p.8139-8144
Abstract
Two series of C3-benzamido and O2-anion-substituted galactopyranosides were synthesized and studied as binders to arginine-rich proteins galectin-1, -3, -7, -8N (N-terminal domain), and -9N (N-terminal domain). The first series had a 4-methylbenzamide at C3 and the anionic O2-substituent was varied. The second series varied the 4-substituent of the C3-benzamide, whereas the anionic O2 substituent was kept as a sulfate. The influence of the O2-anion substituent correlated negatively with the oxygen charge density in case of galectin-1, -3, and -9N. In the second series, the electron-donating capacity of the 4-substituent of the C3-benzamides correlated positively with the magnitude of the affinity enhancement by the 2O-sulfate.
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
arginine, benzamides, galectins, molecular recognition, structure-activity relationships
in
Chemistry: A European Journal
volume
17
issue
29
pages
8139 - 8144
publisher
Wiley-Blackwell
external identifiers
  • wos:000293702500024
  • pmid:21656580
  • scopus:79960005620
  • pmid:21656580
ISSN
1521-3765
DOI
10.1002/chem.201003247
language
English
LU publication?
yes
id
bac0bf18-f858-49de-88f5-4ec24611d435 (old id 2008301)
date added to LUP
2016-04-04 09:44:51
date last changed
2023-02-21 11:41:37
@article{bac0bf18-f858-49de-88f5-4ec24611d435,
  abstract     = {{Two series of C3-benzamido and O2-anion-substituted galactopyranosides were synthesized and studied as binders to arginine-rich proteins galectin-1, -3, -7, -8N (N-terminal domain), and -9N (N-terminal domain). The first series had a 4-methylbenzamide at C3 and the anionic O2-substituent was varied. The second series varied the 4-substituent of the C3-benzamide, whereas the anionic O2 substituent was kept as a sulfate. The influence of the O2-anion substituent correlated negatively with the oxygen charge density in case of galectin-1, -3, and -9N. In the second series, the electron-donating capacity of the 4-substituent of the C3-benzamides correlated positively with the magnitude of the affinity enhancement by the 2O-sulfate.}},
  author       = {{Öberg, Christopher T. and Noresson, Ann Louise and Leffler, Hakon and Nilsson, Ulf J.}},
  issn         = {{1521-3765}},
  keywords     = {{arginine; benzamides; galectins; molecular recognition; structure-activity relationships}},
  language     = {{eng}},
  number       = {{29}},
  pages        = {{8139--8144}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry: A European Journal}},
  title        = {{Arene-anion based arginine-binding motif on a galactose scaffold : Structure-activity relationships of interactions with arginine-rich galectins}},
  url          = {{http://dx.doi.org/10.1002/chem.201003247}},
  doi          = {{10.1002/chem.201003247}},
  volume       = {{17}},
  year         = {{2011}},
}