Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides.
Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxazolidinones.
Elenkov
Maja Majerić
MM
Ruder Bosković Institute, Zagreb, Croatia.
Tang
Lixia
L
Meetsma
Auke
A
Hauer
Bernhard
B
Janssen
Dick B
DB
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D006867:Hydrolases / Q000378:metabolism*; D007700:Kinetics; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D012231:Rhizobium / Q000201:enzymology*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D023303:Oxazolidinones; D006867:Hydrolases; C430848:halohydrin dehalogenase