Yaping Xue, Yuguo Zheng, Zhi-qiang Liu
Aug 7, 2014
Citations
0
Influential Citations
18
Citations
Journal
ACS Catalysis
Abstract
Enantiopure non-natural 2-aryl-amino acids are important intermediates for synthesizing pharmaceuticals. To develop an efficient chemoenzymatic process to produce non-natural 2-aryl-amino acids, a penicillin G acylase (PGA) gene from Bacillus megaterium was cloned and expressed in Bacillus subtilis WB800. The recombinant PGA exhibited a high hydrolytic activity and excellent enantioselectivity (E > 200) toward N-phenylacetyl derivatives of non-natural 2-aryl-amino acids. The l-2-aryl-amino acids were obtained in >99.9% enantiomeric excess (ee) and >49% conversion within 3 h. The position and type of the substituent in the substrate influence the recombinant PGA activity but do not affect the PGA enantioselectivity. The kinetic parameters of the recombinant PGA for different substrates were determined and compared. The mechanisms of enantioselectivity of PGA with respect to different substrates were elucidated. The chiral discrimination of PGA with respect to rac-2a–e was mainly because the d-substrates us...