title: Bacterial preparation of enantiopure unactivated aziridine-2-carboxamides and their transformation into enantiopure nonnatural amino acids and vic-diamines.
abstract: [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.
authors.affiliation: Departamento de Química OrgAnica e InorgAnica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33071 Oviedo, Spain.
authors.forename: Roberto
authors.initials: R
authors.lastname: Moran-Ramallal
authors.forename: Ramón
authors.initials: R
authors.lastname: Liz
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
mesh_terms: 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
chemical_list: D000596:Amino Acids; D001388:Aziridines; D001593:Benzyl Compounds; D001688:Biological Products; D003959:Diamines; C518574:aziridine-2-carboxamide; D012694:Serine; C033132:aziridine