The α-chymotrypsin-catalyzed Povarov reaction: one-pot synthesis of tetrahydroquinoline derivatives

Abstract

The three-component one-pot Povarov reaction for the synthesis of tetrahydroquinoline derivatives was catalyzed by α-chymotrypsin from bovine pancreas (BPC) for the first time. The products were obtained in moderate to good yields with a wide range of substrates. Based on the control and comparison experiments of natural and promiscuous activities, a tentative mechanism was discussed. Molecular docking and energy calculation of quantum chemistry were used to explain the experimental results in theory. As a novel case of enzyme catalytic promiscuity, this work expands the application of BPC. Exploring the untapped catalytic promiscuity of natural enzymes may also provide useful information about enzyme evolution.