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

Summary, in English

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: Christopher Öberg; Hakon Leffler; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis; Division of Microbiology, Immunology and Glycobiology - MIG
• Publishing year: 2008
• Language: English
• Pages: 2297-2301
• Publication/Series: Journal of Medicinal Chemistry
• Volume: 51
• Issue: 7
• Links: http://dx.doi.org/10.1021/jm701266y
• Document type: Journal article
• Publisher: The American Chemical Society (ACS)
• Topic: Medicinal Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 1520-4804