Bacterial preparation of enantiopure unactivated aziridine-2-carboxamides and their transformation into enantiopure nonnatural amino acids and vic-diamines.
[reaction: see text] Enantiopure (1R,2S)-1-benzyl- and 1-arylaziridine-2-carboxamides were obtained by kinetic resolution of their racemates by Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis. Several regio- and enantioselective nucleophilic ring openings of (1R,2S)-1-benzylaziridine-2-carboxamide or its LAH-reduced product led to a series of enantiopure products, such as O-methyl-l-serine and some vicinal diamines.
Moran-Ramallal
Roberto
R
Departamento de Química OrgAnica e InorgAnica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33071 Oviedo, Spain.
Liz
Ramón
R
Gotor
Vicente
V
D000596:Amino Acids / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis*; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D001688:Biological Products / Q000737:chemistry; D001711:Biotransformation; D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis; D006868:Hydrolysis; D007700:Kinetics; D008956:Models, Chemical; D012240:Rhodococcus / Q000201:enzymology*; D012694:Serine / Q000031:analogs & derivatives; D013237:Stereoisomerism
D000596:Amino Acids; D001388:Aziridines; D001593:Benzyl Compounds; D001688:Biological Products; D003959:Diamines; C518574:aziridine-2-carboxamide; D012694:Serine; C033132:aziridine