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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
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Medicinal Chemistry
volume
51
issue
7
pages
2297 - 2301
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:18318467
  • wos:000254709100035
  • scopus:41849118385
ISSN
1520-4804
DOI
10.1021/jm701266y
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: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)
id
04efa8fd-9508-4fdc-8f40-5d1c5fdaf6c2 (old id 1052829)
date added to LUP
2016-04-01 12:02:08
date last changed
2022-01-26 21:50:46
@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    = {{The 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}},
  doi          = {{10.1021/jm701266y}},
  volume       = {{51}},
  year         = {{2008}},
}