title: Arene-anion based arginine-binding motif on a galactose scaffold: structure-activity relationships of interactions with arginine-rich galectins.
abstract: Two series of C3-benzamido and O2-anion-substituted galactopyranosides were synthesized and studied as binders to arginine-rich proteins galectin-1, -3, -7, -8N (N-terminal domain), and -9N (N-terminal domain). The first series had a 4-methylbenzamide at C3 and the anionic O2-substituent was varied. The second series varied the 4-substituent of the C3-benzamide, whereas the anionic O2 substituent was kept as a sulfate. The influence of the O2-anion substituent correlated negatively with the oxygen charge density in case of galectin-1, -3, and -9N. In the second series, the electron-donating capacity of the 4-substituent of the C3-benzamides correlated positively with the magnitude of the affinity enhancement by the 2O-sulfate.
authors.affiliation: Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Öberg
authors.forename: Ann-Louise
authors.initials: AL
authors.lastname: Noresson
authors.forename: Hakon
authors.initials: H
authors.lastname: Leffler
authors.forename: Ulf J
authors.initials: UJ
authors.lastname: Nilsson
mesh_terms: D000818:Animals; D000838:Anions / Q000737:chemistry; D001120:Arginine / Q000378:metabolism*; D001549:Benzamides / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D037161:Galectins / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D011485:Protein Binding; D017434:Protein Structure, Tertiary; D013329:Structure-Activity Relationship
chemical_list: D000838:Anions; D001549:Benzamides; D037161:Galectins; D001120:Arginine; D005690:Galactose