Effect of molecular imprinting on the enzymatic enantioselective ammonoLysis of phenylglycine methyl ester

摘要

Enzymatic ammonolysis is a novel reaction which was discovered in the mid of 1990s. This reaction not only provides an useful method for the preparation of functional amides, but also can be effectively used in the resolution of chiral compounds. R-phenylglycine and its derivatives are key intermediates in the manufacture of β-lactam antibiotics. Many efforts have been put into enzymatic production of these important compounds. We have explored the possibility to apply enzymatic enantioselective ammonolysis to the preparation of optically pure R-phenylglycine amide and its derivatives. Effects of reaction conditions and additives on this reaction have been studied. In this paper, we report the improvement of enzymatic enantioselectivity and activity by molecular imprinting of the Ilpase. HPLC equipped with a chiral column OD(Daicel Chemical Industries, LTD)) and a UV detector was used to follow the change of the concentration of racemic substrate, from which the reaction rate and enantioselectivity(ee%) could be obtained.