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J Med Chem. 2008 Apr 10;51(7):2297-301. doi: 10.1021/jm701266y. Epub 2008 Mar 5.

Arginine binding motifs: design and synthesis of galactose-derived arginine tweezers as galectin-3 inhibitors.

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1
Organic Chemistry, Lund University, SE-221 00 Lund, Sweden.

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.

PMID:
18318467
DOI:
10.1021/jm701266y
[Indexed for MEDLINE]

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