Arene-anion based arginine-binding motif on a galactose scaffold : Structure-activity relationships of interactions with arginine-rich galectins
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/2008301
- author
- Öberg, Christopher T. LU ; Noresson, Ann Louise LU ; Leffler, Hakon LU and Nilsson, Ulf J. LU
- organization
- publishing date
- 2011
- 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}}, }