Microbiological transformations. 47. A step toward a green chemistry preparation of enantiopure (S)-2-, -3-, and -4-pyridyloxirane via an epoxide hydrolase catalyzed kinetic resolution.
The biocatalyzed hydrolytic kinetic resolution of 2-, 3-, and 4-pyridyloxirane by the Aspergillus niger epoxide hydrolase (EH) has been explored. This was used to perform a gram scale preparation of these epoxides of (S) absolute configuration using a process performed at a concentration as high as 10 g/L (82 mM). All three epoxides have been obtained in a nearly enantiopure form (ee > 98%). Interestingly, it was shown that this biotransformation could be achieved using plain water instead of buffer solution, an important improvement as far as downstream processing of an eventual industrial process is concerned. Neither of these substrates could be obtained in reasonable enantiomeric purity and yield using the nowadays most efficient metal-based catalysts.
Genzel
Y
Y
Groupe Biocatalyse et Chimie Fine, ESA 6111 associée au CNRS, Université de la Méditerranée, Faculté des Sciences de Luminy, Case 901, 163 avenue de Luminy, 13288 Marseille, France.
Archelas
A
A
Broxterman
Q B
QB
Schulze
B
B
Furstoss
R
R
D001234:Aspergillus niger / Q000201:enzymology; D002625:Chemistry, Organic / Q000379:methods; D004851:Epoxide Hydrolases / Q000378:metabolism; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007700:Kinetics; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C430855:2-pyridyloxirane; C430857:3-pyridyloxirane; C430856:4-pyridyloxirane; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D011725:Pyridines; D004851:Epoxide Hydrolases