Substrate specificity and product stereochemistry in the dehalogenation of 2-haloacids with the crude enzyme preparation from Pseudomonas putida

Enzyme and Microbial Technology

Volumn 22, Issue 5, 1998, Pages 323-328

  Vyazmensky, Maria ^a   Geresh, Shimona ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

2 haloacid dehalogenase; Immobilization; Organic solvents; Stereoselectivity; Substrate specificity

Indexed keywords

ACETIC ACID; BACTERIA; CATALYST ACTIVITY; CELL IMMOBILIZATION; ENZYME IMMOBILIZATION; ORGANIC SOLVENTS; SUBSTITUTION REACTIONS; SUBSTRATES; SULFUR COMPOUNDS;

CELITE; DIMETHYL SULFOXIDE; DIMETHYLFORMAMIDE; ENZYME SPECIFICITY; HALOACIDS; PROPIONIC ACID;

DEHALOGENATION;

BUFFER; DIMETHYL SULFOXIDE; HALOACID; INFUSORIAL EARTH; N,N DIMETHYLFORMAMIDE; ORGANIC SOLVENT; OXIDOREDUCTASE; PROPIONIC ACID;

ARTICLE; DEHALOGENATION; ENZYME SPECIFICITY; IMMOBILIZED CELL; NONHUMAN; PSEUDOMONAS PUTIDA; STEREOCHEMISTRY; STOICHIOMETRY;

PSEUDOMONAS PUTIDA;

EID: 0032055368     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(97)00181-6     Document Type: Article

References (20)

1. Stevenson, H. A. and Brookes, R. F. α-Phenoxyalkanoic acids. Brit. Pat. 822, 199; Boots Pure Drug Co. Ltd., 1959.
2. Nishiyama, R., Takahiro, H. and Nobuyuki, S. 4-(5-Fluoromethyl-2-pyridyloxy)phenoxy-alkane carboxylic acids, their derivatives, and their use as herbicides. Ger. Offen. 2,812,571, (Cl. C07D213/64) Ishihara Sangyo Kaisha, Ltd., 1979.
3. Taylor S.C. S-2-chloropropanoic acid by biotransformation. Copping L. G., Martin R. E., Pickett J. A., Bucke C., Bunch A. W. Opportunities in Biotransformations. 1990;170-176 Elsevier Appl. Sci. Publ.
4. Motosugi K., Esaki N., Soda K. Purification and properties of a new enzyme, D,L-haloacid dehalogenase, from Pseudomonas sp. J. Bacteriol. 150:1982;522-527.
5. Motosugi K., Esaki N., Soda K. Purification and properties of 2-halo acid dehalogenase from Pseudomonas putida. Agric. Biol. Chem. 46:1982;837-838.
6. Meusel M., Rehm H. J. Biodegradation of dichloracetic acid by freely suspended and adsorptive immobilized Xanthobacter autotrophicus GJ10 in soil. Appl. Microbiol. Biotechnol. 40:1993;165-171.
7. Overmeyer C., Rehm H. J. Biodegradation of 2-chloroethanol by freely suspended and absorbed immobilized Pseudomonas putida US2 in soil. Appl. Microbiol. Biotechnol. 43:1995;143-149.
8. Hisano T., Hata Y., Fujii T., Liu J. Q., Kurihara T., Esaki N., Soda K. Crystallization and preliminary X-ray crystallographic studies of α-2-haloacid dehalogenase from Pseudomonas sp. YL. Proteins Struct. Funct. Genet. 24:1996;520-522.
9. Ridder I. S., Rozeboom I. J., Kingma J., Janssen D. B., Dijkstra B. W. Crystallization and preliminary x-ray analysis of α-2-haloacid dehalogenase from Xanthobacter. Protein Sci. 4:1995;2619-2620.
10. 18O incorporation experiments. J. Biol. Chem. 270:1995;18309-18312.
11. Kohler-Staub D., Kohler H. P. E. Microbial degradation of beta-chlorinated four-carbon aliphatic acids. J. Bacteriol. 171:1989;1428-1434.
12. Asmara W., Murdiyatmo U., Baines A. J., Bull A. T., Hardman D. J. Protein engineering of the 2-haloacid halidohydrolase IVa from Pseudomonas cepacia MBA4. Biochem. J. 292:1993;69-74.
13. Schneider B., Mueller R., Frank R., Lingens F. Site-directed mutagenesis of the 2-haloalkanoic acid dehalogenase I gene from Pseudomonas sp. strain CBS3 and its effect on catalytic activity. Biol. Chem. Hoppe-Seyler. 374:1993;489-496.
14. Hasan A. K. M. Q., Takada H., Esaki N., Soda K. Catalytic action of L-2-halo acid dehalogenase on long-chain L-2-haloalkanoic acids in organic solvents. Biotech. Bioeng. 38:1991;1114-1117.
15. Liu J.-Q., Kurihara T., Quamrul Hasan A. K. M., Nardi-Deiv V., Koshikawa H., Esaki N., 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.
16. Iwasaki J., Utsumi S, Hagino K., Ozawa J. A new spectrophotometric method for the determination of small amounts of chloride using the mercuric thiocyanate method. Bull. Chem. Soc. Jpn. 29:1956;860-864.
17. A. I. Vogel, XVI.6. Determination of water with the Karl Fischer reagent. In: Quantitative Inorganic Analysis (Longmans, Green and Co. Ltd.) 3rd ed., London 1961, 944.
18. Gutmann J., Wahlefeld A. W. L-(+)-lactate:Determination with lactate dehydrogenase and NAD. In: Methods of Enzymatic Analysis, (Hans Ulrich Bergmeyer, ed.) Vol. 3, 2nd ed. Verlag Chemie GmbH, Weinheim, 1974, 1464.
19. Reagents, Tables for the Chemical Laboratory, Merck Darmstadt, Germany, 8-10.
20. Tawaki S., Klibanov A. M. Inversion of enzyme enantioselectivity mediated by the solvent. J. Am. Chem. Soc. 114:1991;1882-1884.