Nitrile and amide biotransformations for the synthesis of enantiomerically pure 3-arylaziridine-2-carboxamide derivatives and their stereospecific ring-opening reactions.
Catalyzed by Rhodococcus erythropolis AJ270 (whole cell catalyst) under very mild conditions, a number of racemic trans-3-arylaziridine-2-carbonitriles and amides were efficiently transformed into enantiopure 2R,3S-3-arylaziridine-2-carboxamides. While the nitrile hydratase exhibits low selectivity against nitrile substrates, the amidase is highly enantioselective toward 2S,3R-3-arylaziridine-2-carboxamides. Upon the treatment with catalytic hydrogenation, amine, or water in the presence of one equivalent of TFA, the resulting aziridine-2-carboxamides underwent highly efficient and stereospecific ring-opening reactions to produce enantiopure alpha-amino-, alpha,beta-diamino-, and alpha-amino-beta-hydroxy-propanamide derivatives in high yields.
Wang
Jin-Yuan
JY
Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China.
Wang
De-Xian
DX
Pan
Jie
J
Huang
Zhi-Tang
ZT
Wang
Mei-Xiang
MX
D000577:Amides / Q000737:chemistry / Q000493:pharmacokinetics*; D000588:Amines / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry / Q000493:pharmacokinetics*; D001711:Biotransformation; D002384:Catalysis; D006836:Hydro-Lyases / Q000493:pharmacokinetics*; D006865:Hydrogenation; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry / Q000493:pharmacokinetics*; D012240:Rhodococcus / Q000201:enzymology*; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000577:Amides; D000588:Amines; D001388:Aziridines; D009570:Nitriles; C518574:aziridine-2-carboxamide; D014867:Water; D014269:Trifluoroacetic Acid; D006836:Hydro-Lyases; C048831:nitrile hydratase