Co-host: The Chemical Society of Japan, The Chemical Society of Japan, Kyushu Branch, The Society of Synthetic Organic Chemistry, Japan (Cooperation)
In order to evaluate the effect of the alkyl substituent at the nitrogen atom in amino acids and π-π interactions involving phenylalanine, dipeptides bearing N-methylglycine, N-methylalanine, and para-substituted phenylalanine were synthesized. The hydrolysis of 11 kinds of dipeptides catalyzed by carboxypeptidase Y and carboxypeptidase A was studied. There was found a good linear relationship between Michaelis-Menten constant Km and hydrophobic parameters evaluated by reversed-phase HPLC. Also observed was a good linear relationship between catalytic constant kcat in the enzymatic hydrolysis of the dipeptides and π-π interactions of monosubstituted benzene evaluated by graphitic carbon-phase HPLC.
