Catalytic action of L-2-halo acid dehalogenase on long-chain L-2-haloalkanoic acids in organic solvents |
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Authors: | Hasan A K Takada H Esaki N Soda K |
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Affiliation: | Laboratory of Microbial Biochemistry, Institute for Chemical Research, Kyoto University, Uji, Kyoto-fu 611, Japan. |
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Abstract: | A Lyophilized preparation of L-2-halo acid dehalogenase was not only stable but also catalytically active in anhydrous dimethyl sulfoxide, toluene, and other organic solvents. 2-Halo acids with long alkyl (C(5)-C(16)) or aromatic (phenyl and benzyl) side chains were inert in water but dehalogenated effectively in anhydrous dimethyl sulfoxide by the lyophilized enzyme. Long chain 2-haloalkanoic acids such as 2-bromohexadecanoic acids were better as substrate than short-chain halo acids (e.g., 2-chloropropanoic acid). The dehalogenation proceed with inversion of C(2) configuration to produce the corresponding (2R)-2-hydroxy acids in anhydrous dimethyl sulfoxide in the same way as found in water. |
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Keywords: | L-2-halo acid dehalogenase dehalogenation in dimethyl sulfoxide 2-hydroxy acids stereospecific production of substrate specificity change in organic solvent |
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