Abstract
The occurrence of a new bacterial dehalogenase acting on both the optical isomers of 2-halogenated alkanoic acids was demonstrated. When the haloalkanoic acid-utilizing bacteria were screened in a medium containing dl-2-chloropropionate as a sole carbon source, two types of bacteria were isolated: (1) a few strains utilizing both d- and l-isomers of 2-chloropropionate and (2) strains utilizing only the l-isomer. A dehalogenating enzyme was obtained from the cells of Pseudomonas sp. which is able to utilize both isomers. The crude enzyme catalyzed the dehalogenation of d- and l-2-chloropropionates to yield l- and d-isomers of lactate, respectively. The enzyme showed the same pH optimum and heat inactivation rate for the d- and l-isomers. Apparent K m values for d- and l-2-chloropropionates were 4.5 and 1.0 mM, respectively. The enzyme acted specifically on 2-haloalkanoic acids. Activity staining of disc-gels electrophoresed witg the crude enzyme preparation showed that the dehalogenation of d- and l-2-chloropropionates, monochloroacetate, dichloroacetate, 2,2-dichloropropionate, and dl-2-chlorobutyrate is due to a single protein.
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Abbreviations
- MCA:
-
monochloroacetic acid
- DCA:
-
dichloroacetic acid
- TCA:
-
trichloroacetic acid
- 2 MCPA:
-
2-monochloropropionic acid
- 22 DCPA:
-
2,2-dichloropropionic acid
- 3 MCPA:
-
3-monochloropropionic acid
- 2 MCBA:
-
2-monochlorobutyric acid
- 3 MCBA:
-
3-monochlorobutyric acid
- 4 MCBA:
-
4-monochlorobutyric acid
References
Berry EKM, Allison N, Skinner AJ, Cooper RA (1979) Degradation of the selective herbicide 2,2-dichloropropionate (Dalapon) by a soil bacterium. J Gen Microbiol 110: 39–45
Buchanan RE, Gibbons NE (1974) Bergey's manual of determinative bacteriology, 8th edn. The Williams and Wilkins Co., Baltimore
Davis BJ (1964) Disc electrophoresis. II. Method and application to human serum proteins. Ann NY Acad Sci 121:404–427
Dixon M, Webb EC (1979) Enzymes, 3rd edn. Longman Group Ltd., London, pp 916–917
Fu S-CJ, Birnbaum SM, Greenstein JP (1954) Influence of optically active acyl groups on the enzymatic hydrolysis of N-acylated-l-amino acids. J Am Chem Soc 76:6054–6058
Goldman P, Milne GWA, Keister DB (1968) Carbon-halogen bond cleavage, III. Studies on bacterial halidohydrolase. J Biol Chem 243:428–434
Gornall AG, Bardawill CJ, David MM (1949) Determination of serum proteins by means of the biuret procedure. J Biol Chem 177:751–766
Hardman DJ, Slater JH (1981) Dehalogenases in soil bacteria. J Gen Microbiol 123:117–128
Hirsch P, Alexander M (1960) Microbial decomposition of halogenated propionic and acetic acids. Can J Microbiol 6:241–249
Iwasaki I, Utsumi S, Hagino K, Ozawa T (1956) A new spectrophotometric method for the determination of small amounts of chloride using the mercuric thiocyanate method. Bull Chem Soc Jpn 29:860–864
Jensen HL (1960) Decomposition of chloroacetates and chloropropionates by bacteria. Acta Agr Scand 10:83–103
Jensen HL (1963) Carbon nutrition of some microorganisms decomposing halogen-substituted aliphatic acids. Acta Agr Scand 13:404–412
Kawasaki H, Tone N, Tonomura K (1981) Plasmid-determined dehalogenation of haloacetates in Moraxella species. Agr Biol Chem 45:29–34
Little M, Williams PA (1971) A bacterial halidohydrolase. Its purification, some properties and its modification by specific amino acid reagents. Eur J Biochem 21:99–109
Macgregor AN (1963) The decomposition od dichloropropionate by soil micro-organisms. J Gen Microbiol 30:497–501
Magee LA, Colmer AR (1959) Decomposition of 2,2-dichloropropionic acid by soil bacteria. Can J Microbiol 5:255–260
Senior E, Bull AT, Slater JH (1976) Enzyme evolution in a microbial community growing on the herbicide Dalapon, vol 263. Nature, London, pp 476–479
Stanier RY, Palleroni NJ, Doudoroff M (1966) The aerobic pseudomonads: a taxonomic study. J Gen Microbiol 43:159–271
Tonomura K, Futai F, Tanabe O, Yamaoka T (1965) Dettuorination of monofluoroacetate by bacteria, Part I. Isolation of bacteria and their activity of defluorination. Agr Biol Chem 29:124–128
Weightman AJ, Slater JH (1980) Selection of Pseudomonas putida strains with elevated dehalogenase activities by continuous culture growth on chlorinated alkanoic acids. J Gen Microbiol 121:187–193
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Motosugi, K., Esaki, N. & Soda, K. Bacterial assimilation of d- and l-2-chloropropionates and occurrence of a new dehalogenase. Arch. Microbiol. 131, 179–183 (1982). https://doi.org/10.1007/BF00405875
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DOI: https://doi.org/10.1007/BF00405875