BioChem - DOS

Light-driven kinetic resolution of α-functionalized carboxylic acids enabled by an engineered fatty acid photodecarboxylase

Angewandte Chemie. international edition

Xu, Jian; Hu, Yujing; Fan, Jiajie; Arkin, Mamatjan; Li, Danyang; Peng, Yongzhen; Xu, Weihua; Lin, Xianfu; Wu, Qi

<P><B>Abstract</B></P><P>Chiral &alpha;&#8208;functionalized carboxylic acids are valuable precursors for a variety of medicines and natural products. Herein, we described an engineered fatty acid photodecarboxylase (<I>Cv</I>FAP)&#8208;catalyzed kinetic resolution of &alpha;&#8208;amino acids and &alpha;&#8208;hydroxy acids, which provides the unreacted <I>R</I>&#8208;configured substrates with high yields and excellent stereoselectivity (<I>ee</I> up to 99 %). This efficient light&#8208;driven process requires neither NADPH recycling nor prior preparation of esters, which were required in previous biocatalytic approaches. The structure&#8208;guided engineering strategy is based on the scanning of large amino acids at hotspots to narrow the substrate binding tunnel. To the best of our knowledge, this is the first example of asymmetric catalysis by an engineered <I>Cv</I>FAP.</P>

2019

1433-7851

1521-3773

58

25

pp.8474-8478

10.1002/anie.201903165

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART97256206

biocatalysis; kinetic resolution; photoenzymes; rational design; α-functionalized carboxylic acids