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.

• Författare: Christopher Öberg; Hakon Leffler; Ulf Nilsson
• Avdelning/ar: Centrum för analys och syntes; Avdelningen för mikrobiologi, immunologi och glykobiologi - MIG
• Publiceringsår: 2008
• Språk: Engelska
• Sidor: 2297-2301
• Publikation/Tidskrift/Serie: Journal of Medicinal Chemistry
• Volym: 51
• Issue: 7
• Länkar: http://dx.doi.org/10.1021/jm701266y
• Dokumenttyp: Artikel i tidskrift
• Förlag: The American Chemical Society (ACS)
• Ämne: Medicinal Chemistry
• Status: Published
• ISBN/ISSN/Övrigt: ISSN: 1520-4804