Improved catalytic properties of halohydrin dehalogenase by modification of the halide-binding site

Biochemistry

Volumn 44, Issue 17, 2005, Pages 6609-6618

  Tang, Lixia ^a   Torres Pazmiño, Daniel E ^a   Fraaije, Marco W ^a   De Jong, René M ^a   Dijkstra, Bauke W ^a   Janssen, Dick B ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DEHALOGENATION; ENZYMES; HYDROGEN BONDS; PROTONS; REACTION KINETICS;

HALIDE BINDING; HALIDE IONS; INTRAMOLECULAR SUBSTITUTIONS; VICINAL HALOALCOHOLS;

BIOCHEMISTRY;

BACTERIAL ENZYME; HALOHYDRIN DEHALOGENASE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CATALYSIS; CONTROLLED STUDY; ENANTIOSELECTIVITY; GENE MUTATION; HYDROGEN BOND; KINETICS; MUTAGENESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; RHIZOBIUM RADIOBACTER; STEADY STATE; WILD TYPE; X RAY ANALYSIS;

ASPARAGINE; BACTERIAL PROTEINS; BINDING SITES; BROMIDES; CATALYTIC DOMAIN; CHLORIDES; HYDROLASES; KINETICS; LIGANDS; MUTAGENESIS, SITE-DIRECTED; PHENYLALANINE; PROTEIN BINDING; RHIZOBIUM; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM; TRYPTOPHAN; TYROSINE;

AGROBACTERIUM TUMEFACIENS; RADIOBACTER;

EID: 17844391799     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi047613z     Document Type: Article

References (31)

1. Lutje Spelberg, J. H., van Hylckama Vlieg, J. E. T., Tang, L., Janssen, D. B., and Kellogg, R. M. (2001) Highly enantioselective and regioselective biocatalytic azidolysis of aromatic epoxides, Org. Lett. 3, 41-43.
2. Lutje Spelberg, J. H., Tang, L., van Gelder, M., Kellogg, R. M., and Janssen, D. B. (2002) Exploration of the biocatalytic potential of a halohydrin dehalogenase using chromogenic substrates, Tetrahedron: Asymmetry 13, 1083-1089.
3. van den Wijngaard, A. J., Janssen, D. B., and Witholt, B. (1989) Degradation of epichlorohydrin and halohydrins by bacterial cultures isolated from freshwater sediment, J. Gen. Microbiol. 135, 2199-2208.
4. Nakamura, T., Nagasawa, T., Yu, F., Watanabe, I., and Yamada, H. (1991) A new catalytic function of halohydrin hydrogen-halidelyase, synthesis of β-hydroxynitriles from epoxides and cyanide, Biochem. Biophys. Res. Commun. 180, 124-130.
5. Poelarends, G. J., van Hylckama Vlieg, J. E. T., Marchesi, J. R., Freitas dos Santos, L. M., and Janssen, D. B. (1999) Degradation of 1,2-dibromoethane by Mycobacterium sp. strain GP1, J. Bacteriol. 181, 2050-2058.
6. Marek, J., Vevodova, J., Smatanova, I. K., Nagata, Y., Svensson, L. A., Newman, J., Takagi, M., and Damborsky, J. (2000) Crystal structure of the haloalkane dehalogenase from Sphingomonas paucimobilis UT26, Biochemistry 39, 14082-14086.
7. Newman, J., Peat, T. S., Richard, R., Kan, L., Swanson, P. E., Affholter, J. A., Holmes, I. H., Schindler, J. F., Unkefer, C. J., and Terwilliger, T. C. (1999) Haloalkane dehalogenases: Structure of a Rhodococcus enzyme, Biochemistry 38, 16105-16114.
8. Ridder, I. S., Rozeboom, H. J., Kalk, K. H., and Dijkstra, B. W. (1999) Crystal structures of intermediates in the dehalogenation of haloalkanoates by L-2-haloacid dehalogenase, J. Biol. Chem. 274, 30672-30678.
9. Verschueren, K. H., Seljee, F., Rozeboom, H. J., Kalk, K. H., and Dijkstra, B. W. (1993) Crystallographic analysis of the catalytic mechanism of haloalkane dehalogenase, Nature 363, 693-698.
10. Benning, M. M., Taylor, K. L., Liu, R.-Q., Yang, G., Xiang, H., Wesenberg, G., Dunaway-Mariano, D., and Holden, H. M. (1996) Structure of 4-chlorobenzoyl coenzyme A dehalogenase determined to 1.8 Å resolution: an enzyme catalyst generated via adaptive mutation, Biochemistry 35, 8103-8109.
11. de Jong, R. M., and Dijkstra, B. W. (2004) Structure and mechanism of bacterial dehalogenases: different ways to cleave a carbon-halogen bond, Curr. Opin. Struct. Biol. 13, 722-730.
12. Lutje Spelberg, J. H., van Hylckama Vlieg, J. E. T., Bosma, T., Kellogg, R. M., and Janssen, D. B. (1999) A tandem enzyme reaction to produce optically active halohydrins, epoxides and diols, Tetrahedron: Asymmetry 10, 2863-2870.
13. Van Hylckama Vlieg, J. E. T., Tang, L., Lutje Spelberg, J. H., Smilda, T., Poelarends, G. J., Bosma, T., van Merode, A. E. J., and Janssen, D. B. (2001) Halohydrin dehalogenases are structurally and mechanistically closely related to short-chain dehydrogenases/reductases, J. Bacteriol. 183, 5058-5066.
14. de Jong, R. M., Tiesinga, J. J. W., Rozeboom, H. J., Kalk, K. H., Tang, L., Janssen, D. B., and Dijkstra, B. W. (2003) Structure and mechanism of a bacterial haloalcohol dehalogenase: a new variation of the short-chain dehydrogenase/reductase fold without an NAD(P)H binding site, EMBO J. 22, 4933-4944.
15. Jörnvall, H., Persson, B., Krook, M., Atrian, S., Gonzalez-Duarte, R., Jeffery, J., and Ghosh, D. (1995) Short-chain dehydrogenases/reductases (SDR), Biochemistry 34, 6003-6013.
16. Hwang, C. C., Chang, Y. H., Hsu, C. N., Hsu, H. H., Li, C. W., and Pon, H. I. (2004) Mechanistic roles of Ser114, Tyr155 and Lys159 in 3α-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testossteroni, J. Biol. Chem. (in press).
17. Tang, L., Lutje Spelberg, J. H., Fraaije, M. W., and Janssen, D. B. (2003) Kinetic mechanism and enantioselectivity of halohydrin dehalogenase from Agrobacterium radiobacter, Biochemistry 42, 5378-5386.
18. Tang, L., van Merode, A. E. J., Lutje Spelberg, J. H., Fraaije, M. W., and Janssen, D. B. (2003) Steady-state kinetics and tryptophan fluorescence properties of halohydrin dehalogenase from Agrobacterium radiobacter. Roles of W139 and W249 in the active site and halide-induced conformational change, Biochemistry 42, 14057-14065.
19. Westkaemper, R. B., and Hanzlik, R. P. (1981) Mechanistic studies of epoxide hydrolase utilizing a continuous spectrophotometric assay, Arch. Biochem. Biophys. 208, 195-204.
20. Rink, R., Fennema, M., Smids, M., Dehmel, U., and Janssen, D. B. (1997) Primary structure and catalytic mechanism of epoxide hydrolase from Agrobacterium radiobacter AD1, J. Biol. Chem. 272, 14650-14657.
21. Tang, L., Van Hylckama Vlieg, J. E. T., Lutje Spelberg, J. H., Fraaije, M. W., and Janssen, D. B. (2002) Improved stability of halohydrin dehalogenase from Agrobacterium radiobacter AD1 by replacement of cysteine residues, Enzyme Microb. Technol. 30, 251-258.
22. Bergmann, J. G., and Sanik, J. (1957) Determination of trace amounts of chlorine in naphtha, Anal. Chem. 29, 241-243.
23. Johnson, K. A. (1992) The Enzymes (Boyer, P. D., Ed.) 4th ed., Vol. 20, pp 1-60, Academic Press, New York.
24. Huang, C. Y. (1979) Derivation of initial velocity and isotope exchange rate equations, Methods Enzymol. 63, 54-84.
25. Johnson, K. A. (1986) Rapid kinetic analysis of mechanochemical adenosine-triphosphatases, Methods Enzymol. 134, 677-705.
26. Schanstra, J. P., and Janssen, D. B. (1996) Kinetics of halide release of haloalkane dehalogenase: evidence for a slow conformational change, Biochemistry 35, 5624-5632.
27. Pries, F., Van den Wijngaard, A. J., Bos, R., Pentenga, M., and Janssen, D. B. (1994) The role of spontaneous cap domain mutations in haloalkane dehalogenase specificity and evolution, J. Biol. Chem. 269, 17490-17494.
28. Rüdiger, M., and Oesterhelt, D. (1997) Specific arginine and threonine residues control anion binding and transport in the light-driven chloride pump halorhodopsin, EMBO J. 16, 3813-3821.
29. Schanstra, J. P., Ridder, A., Kingma, J., and Janssen, D. B. (1997) Influence of mutations of Val226 on the catalytic rate of haloalkane dehalogenase, Protein Eng. 10, 53-61.
30. Rotticci, D., Rotticci-Mulder, J. C., Denman, S., Norin, T., and Hult, K. (2001) Improved enantioselectivity of a lipase by rational protein engineering, ChemBioChem 2, 766-770.
31. Chen-Goodspeed, M., Sogorb, M. A., Wu, F., and Raushel, F. M. (2001) Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues, Biochemistry 40, 1332-1339.