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Light‐Driven Kinetic Resolution of α‐Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase
Author(s) -
Xu Jian,
Hu Yujing,
Fan Jiajie,
Arkin Mamatjan,
Li Danyang,
Peng Yongzhen,
Xu Weihua,
Lin Xianfu,
Wu Qi
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903165
Subject(s) - kinetic resolution , chemistry , substrate (aquarium) , catalysis , amino acid , carboxylic acid , stereoselectivity , combinatorial chemistry , fatty acid , organic chemistry , enantioselective synthesis , biochemistry , biology , ecology
Chiral α‐functionalized carboxylic acids are valuable precursors for a variety of medicines and natural products. Herein, we described an engineered fatty acid photodecarboxylase ( Cv FAP)‐catalyzed kinetic resolution of α‐amino acids and α‐hydroxy acids, which provides the unreacted R ‐configured substrates with high yields and excellent stereoselectivity ( ee up to 99 %). This efficient light‐driven process requires neither NADPH recycling nor prior preparation of esters, which were required in previous biocatalytic approaches. The structure‐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 Cv FAP.