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Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors.

Öberg, Christopher LU ; Leffler, Hakon LU and Nilsson, Ulf LU (2008) In Journal of Medicinal Chemistry 51(7). p.2297-2301
Abstract
Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta- d-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide and O2 anionic substituents in that the benzamide stacked face-to-face and the anionic O2 substituent ion-paired with the guanidinium moiety.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Medicinal Chemistry
volume
51
issue
7
pages
2297 - 2301
publisher
American Chemical Society (ACS)
external identifiers
  • pmid:18318467
  • wos:000254709100035
  • scopus:41849118385
ISSN
1520-4804
DOI
10.1021/jm701266y
language
English
LU publication?
yes
id
04efa8fd-9508-4fdc-8f40-5d1c5fdaf6c2 (old id 1052829)
date added to LUP
2008-07-11 09:22:54
date last changed
2017-04-09 03:35:27
@article{04efa8fd-9508-4fdc-8f40-5d1c5fdaf6c2,
  abstract     = {Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta- d-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide and O2 anionic substituents in that the benzamide stacked face-to-face and the anionic O2 substituent ion-paired with the guanidinium moiety.},
  author       = {Öberg, Christopher and Leffler, Hakon and Nilsson, Ulf},
  issn         = {1520-4804},
  language     = {eng},
  number       = {7},
  pages        = {2297--2301},
  publisher    = {American Chemical Society (ACS)},
  series       = {Journal of Medicinal Chemistry},
  title        = {Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors.},
  url          = {http://dx.doi.org/10.1021/jm701266y},
  volume       = {51},
  year         = {2008},
}