1. Highly enantioselective and regioselective biocatalytic azidolysis of aromatic epoxides.
- Author
-
Spelberg JH, van Hylckama Vlieg JE, Tang L, Janssen DB, and Kellogg RM
- Subjects
- Azides chemistry, Catalysis, Epoxy Compounds chemistry, Molecular Structure, Stereoisomerism, Styrenes chemistry, Substrate Specificity, Azides metabolism, Epoxy Compounds metabolism, Hydrocarbons, Aromatic chemistry, Hydrolases metabolism, Rhizobium enzymology, Styrenes metabolism
- Abstract
[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.
- Published
- 2001
- Full Text
- View/download PDF