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  • Title: Nitrile biotransformations for highly efficient and enantioselective syntheses of electrophilic oxiranecarboxamides.
    Author: Wang MX, Lin SJ, Liu CS, Zheng QY, Li JS.
    Journal: J Org Chem; 2003 May 30; 68(11):4570-3. PubMed ID: 12762774.
    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.
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