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  • Title: Highly efficient and enantioselective biotransformations of β-lactam carbonitriles and carboxamides and their synthetic applications.
    Author: Leng DH, Wang DX, Huang ZT, Wang MX.
    Journal: Org Biomol Chem; 2010 Oct 21; 8(20):4736-43. PubMed ID: 20721414.
    Abstract:
    Catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase and amidase containing microbial whole cell catalyst, a number of racemic 1-arylmethyl- and 1-allyl-4-oxoazetidine-2-carbonitriles and carboxamides underwent efficient transformations under very mild conditions to produce enantiopure functionalized S-amide and R-acid products in excellent yields. While the nitrile hydratase showed good enzyme activity but virtually no enantioselectivity, the amidase displayed high R-enantioselectivity against almost all amide substrates tested. The synthetic applications of the resulting functionalized chiral β-lactam derivatives were demonstrated by the facile preparation of β-lactam-fused heterocyclic compounds.
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