Highly enantioselective and regioselective biocatalytic azidolysis of aromatic epoxides.
[figure: see text] The halohydrin dehalogenase from Agrobacterium radiobacter AD1 catalyzed the highly enantioselective and beta-regioselective azidolysis of (substituted) styrene oxides. By means of kinetic resolutions the remaining epoxide and the formed azido alcohol could be obtained in very high ee. In a large scale conversion, the decrease in yield and selectivity due to the uncatalyzed chemical side reaction could be overcome by slow addition of azide.
Spelberg
J H
JH
Department of Biochemistry, Groningen Biomolecular Sciences and Biotechnology Institute, and Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
van Hylckama Vlieg
J E
JE
Tang
L
L
Janssen
D B
DB
Kellogg
R M
RM
D001386:Azides / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006867:Hydrolases / Q000378:metabolism*; D015394:Molecular Structure; D012231:Rhizobium / Q000201:enzymology*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
D001386:Azides; D004852:Epoxy Compounds; D006841:Hydrocarbons, Aromatic; D013343:Styrenes; D006867:Hydrolases; C430848:halohydrin dehalogenase