Kinetic Mechanism and Enantioselectivity of Halohydrin Dehalogenase fromAgrobacterium radiobacter†
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چکیده
منابع مشابه
Kinetic mechanism and enantioselectivity of halohydrin dehalogenase from Agrobacterium radiobacter.
Halohydrin dehalogenase (HheC) from Agrobacterium radiobacter AD1 catalyzes the reversible intramolecular nucleophilic displacement of a halogen by a hydroxyl group in vicinal haloalcohols, producing the corresponding epoxides. The enzyme displays high enantioselectivity toward some aromatic halohydrins. To understand the kinetic mechanism and enantioselectivity of the enzyme, steady-state and ...
متن کاملSequential kinetic resolution catalyzed by halohydrin dehalogenase.
A sequential kinetic resolution catalyzed by halohydrin dehalogenase was employed for the synthesis of two valuable enantiopure building blocks. Resolution of methyl 4-chloro-3-hydroxybutanoate methylester ((R,S)-2) with use of a Trp249Phe mutant of halohydrin dehalogenase yielded methyl 4-cyano-3-hydroxybutanoate methylester ((S)-4) with 96.8% ee (40% yield) and (S)-2 with 95.2% ee (41% yield)...
متن کاملEnantioselective formation and ring-opening of epoxides catalysed by halohydrin dehalogenases.
Halohydrin dehalogenases catalyse the conversion of vicinal halohydrins into their corresponding epoxides, while releasing halide ions. They can be found in several bacteria that use halogenated alcohols or compounds that are degraded via halohydrins as a carbon source for growth. Biochemical and structural studies have shown that halohydrin dehalogenases are evolutionarily and mechanistically ...
متن کاملCatalytic activity of halohydrin dehalogenases towards spiroepoxides.
A novel activity of halohydrin dehalogenases towards spiroepoxides has been found. The enzyme from Arthrobacter sp. (HheA) catalysed highly regioselective azidolysis of spiroepoxides containing 5, 6 and 7-membered cycloalkane rings, while the enzyme from Agrobacterium radiobacter (HheC), besides high regioselectivity, also displayed moderate to high enantioselectivity (E up to >200) that can be...
متن کاملHighly 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 c...
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ژورنال
عنوان ژورنال: Biochemistry
سال: 2003
ISSN: 0006-2960,1520-4995
DOI: 10.1021/bi0273361