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Issue 20, 2010
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Highly efficient and enantioselective biotransformations of β-lactam carbonitriles and carboxamides and their synthetic applications

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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.

Graphical abstract: Highly efficient and enantioselective biotransformations of β-lactam carbonitriles and carboxamides and their synthetic applications

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Article information


Submitted
02 Jun 2010
Accepted
08 Jul 2010
First published
19 Aug 2010

Org. Biomol. Chem., 2010,8, 4736-4743
Article type
Paper

Highly efficient and enantioselective biotransformations of β-lactam carbonitriles and carboxamides and their synthetic applications

D. Leng, D. Wang, Z. Huang and M. Wang, Org. Biomol. Chem., 2010, 8, 4736
DOI: 10.1039/C0OB00198H

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