Synthesis and binding studies of carboxylate binding pocket analogs of vancomycin

Synthetic receptors based on the carboxylate binding pocket of vancomycin were synthesized. Using a UV binding assay, affinities of various cell wall related carboxylates were measured in organic solvents. Affinities in the 103–104 M−1 range were determined as well as almost equal affinities for acylated alanine and lactate. Introduction of additional hydrogen bonding donors or positive charges into the receptors led to increased affinities for the carboxylates.