Reaction: (1) (S)-2-haloacid + H2O = (R)-2-hydroxyacid + halide
(2) (R)-2-haloacid + H2O = (S)-2-hydroxyacid + halide
For diagram click here.
Other name(s): 2-haloalkanoic acid dehalogenase; 2-haloalkanoid acid halidohydrolase; DL-2-haloacid dehalogenase; DL-2-haloacid dehalogenase (inversion of configuration); DL-2-haloacid halidohydrolase (inversion of configuration); DL-DEXi; (R,S)-2-haloacid dehalogenase (configuration-inverting)
Systematic name: (S)-2-haloacid dehalogenase (configuration-inverting)
Comments: Dehalogenates both (S)- and (R)-2-haloalkanoic acids to the corresponding (R)- and (S)-hydroxyalkanoic acids, respectively, with inversion of configuration at C-2. The enzyme from Pseudomonas sp. 113 acts on 2-haloalkanoic acids whose carbon chain lengths are five or less. [See also EC 3.8.1.2 (S)-2-haloacid dehalogenase, EC 3.8.1.9 (R)-2-haloacid dehalogenase and EC 3.8.1.11 2-haloacid dehalogenase (configuration-retaining)]
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, PDB, CAS registry number:
References:
1. Motosugi, K., Esahi, N. and Soda, K. Bacterial assimilation of D- and L-2-chloropropionates and occurrence of a new dehalogenase. Arch. Microbiol. 131 (1982) 179-183. [PMID: 7103659]
2. Motosugi, K., Esahi, N. and Soda, K. Purification and properties of a new enzyme, DL-2-haloacid dehalogenase, from Pseudomonas sp. J. Bacteriol. 150 (1982) 522-527. [PMID: 7068529]
3. Motosugi, K., Esahi, N. and Soda, K. Enzymatic preparation of D- and L-lactic acid from racemic 2-chloropropionic acid. Biotechnol. Bioeng. 26 (1984) 805-806.
4. Kurihara, T., Esaki, N. and Soda, K. Bacterial 2-haloacid dehalogenases: structures and reaction mechanisms. J. Mol. Catal., B Enzym. 10 (2000) 57-65.
5. Liu, J.-Q., Kurihara, T., Hasan, A.K.M.Q., Nardi-Dei, V., Koshikawa, H., Esaki, N. and Soda, K. Purification and characterization of thermostable and nonthermostable 2-haloacid dehalogenases with different stereospecificities from Pseudomonas sp. strain YL. Appl. Environ. Microbiol. 60 (1994) 2389-2393. [PMID: 8074519]
6. Cairns, S.S., Cornish, A. and Cooper, R.A. Cloning, sequencing and expression in Escherichia coli of two Rhizobium sp. genes encoding haloalkanoate dehalogenases of opposite stereospecificity. Eur. J. Biochem. 235 (1996) 744-749. [PMID: 8654424]
7. Leigh, J.A., Skinner, A.J. and Cooper, R.A. Partial purification, stereospecificity and stoichiometry of three dehalogenases from a Rhizobium species. FEMS Microbiol. Lett. 49 (1988) 353-356.
8. Weightman, A.J., Weightman, A.L. and Slater, J.H. Stereospecificity of 2-monochloropropionate dehalogenation by the two dehalogenases of Pseudomonas P3: evidence for two different dehalogenation mechanisms. J. Gen. Microbiol. 128 (1982) 1755-1762. [PMID: 7142958]
9. Soda, K., Kurihara, T., Liu, J.-Q., Nardi-Dei, V., Park, C., Miyagi, M., Tsunasawa, S. and Esaki, N. Bacterial 2-haloacid dehalogenases: Structures and catalytic properties. Pure Appl. Chem. 68 (1996) 2097-2103.