Highly efficient and enantioselective biotransformations of ß-lactam carbonitriles and carboxamides and their synthetic applications.
Org Biomol Chem
; 8(20): 4736-43, 2010 Oct 21.
Article
em En
| MEDLINE
| ID: mdl-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 ß-lactam derivatives were demonstrated by the facile preparation of ß-lactam-fused heterocyclic compounds.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Beta-Lactamas
/
Amidas
/
Nitrilas
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article