title: Nitrile biotransformations for highly efficient and enantioselective syntheses of electrophilic oxiranecarboxamides.
abstract: Catalyzed by a nitrile hydratase/amidase-containing microbial Rhodococcus sp. AJ270 whole-cell catalyst, a number of racemic trans-2,3-epoxy-3-arylpropanenitriles 1 underwent rapid and efficient hydrolysis under very mild conditions to afford 2R,3S-2-arylglycidamides 2 in excellent yield with enantiomeric excess higher than 99.5%. The overall enantioselectivity of the biotransformations originated from the combined effects of a dominantly high 2S-enantioselective amidase and low 2S-enantioselective nitrile hydratase involved in the cell. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects.
authors.affiliation: Laboratory for Chemical Biology, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China. mxwang@iccas.ac.cn
authors.forename: Mei-Xiang
authors.initials: MX
authors.lastname: Wang
authors.forename: Shuang-Jun
authors.initials: SJ
authors.lastname: Lin
authors.forename: Chu-Sheng
authors.initials: CS
authors.lastname: Liu
authors.forename: Qi-Yu
authors.initials: QY
authors.lastname: Zheng
authors.forename: Ji-Sheng
authors.initials: JS
authors.lastname: Li
mesh_terms: D000577:Amides / Q000032:analysis / Q000138:chemical synthesis*; D001711:Biotransformation; D002384:Catalysis; D005027:Ethylene Oxide / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis*; D006836:Hydro-Lyases / Q000378:metabolism*; D007700:Kinetics; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D012240:Rhodococcus / Q000201:enzymology*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D009570:Nitriles; D006836:Hydro-Lyases; C048831:nitrile hydratase; D005027:Ethylene Oxide