Advanced

Arene-Anion Based Arginine-Binding Motif on a Galactose Scaffold: Structure-Activity Relationships of Interactions with Arginine-Rich Galectins.

Oberg, Christopher T; Noresson, Ann-Louise; Leffler, Hakon LU and Nilsson, Ulf J (2011) In Chemistry (Weinheim an der Bergstrasse, Germany) 17. 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.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemistry (Weinheim an der Bergstrasse, Germany)
volume
17
pages
8139 - 8144
publisher
John Wiley & Sons
external identifiers
  • WOS:000293702500024
  • PMID:21656580
  • Scopus:79960005620
ISSN
1521-3765
DOI
10.1002/chem.201003247
language
English
LU publication?
yes
id
bac0bf18-f858-49de-88f5-4ec24611d435 (old id 2008301)
alternative location
http://www.ncbi.nlm.nih.gov/pubmed/21656580?dopt=Abstract
date added to LUP
2011-07-04 13:18:06
date last changed
2017-01-01 07:54:37
@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       = {Oberg, Christopher T and Noresson, Ann-Louise and Leffler, Hakon and Nilsson, Ulf J},
  issn         = {1521-3765},
  language     = {eng},
  pages        = {8139--8144},
  publisher    = {John Wiley & Sons},
  series       = {Chemistry (Weinheim an der Bergstrasse, Germany)},
  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},
  volume       = {17},
  year         = {2011},
}