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Arene–Anion Based Arginine‐Binding Motif on a Galactose Scaffold: Structure–Activity Relationships of Interactions with Arginine‐Rich Galectins
Author(s) -
Öberg Christopher T.,
Noresson AnnLouise,
Leffler Hakon,
Nilsson Ulf J.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003247
Subject(s) - substituent , chemistry , benzamide , galectin , arginine , sulfate , stereochemistry , medicinal chemistry , amino acid , organic chemistry , biochemistry
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.