Highly efficient and enantioselective biotransformations of β-lactam carbonitriles and carboxamides and their synthetic applications.
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.
Leng
Dong-Hui
DH
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Wang
De-Xian
DX
Huang
Zhi-Tang
ZT
Wang
Mei-Xiang
MX
D000577:Amides / Q000737:chemistry*; D000581:Amidohydrolases / Q000378:metabolism; D001711:Biotransformation; D002384:Catalysis; D006836:Hydro-Lyases / Q000378:metabolism; D009570:Nitriles / Q000737:chemistry*; D012240:Rhodococcus / Q000201:enzymology; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry / Q000378:metabolism*
D000577:Amides; D009570:Nitriles; D047090:beta-Lactams; D000581:Amidohydrolases; C019665:amidase; D006836:Hydro-Lyases; C048831:nitrile hydratase