Kinetics and mechanism of oxygen-independent hydrocarbon hydroxylation by ethylbenzene dehydrogenase

Biochemistry

Volumn 46, Issue 25, 2007, Pages 7637-7646

  Szaleniec, Maciej ^a   Hagel, Corina ^b   Menke, Maurycy ^a   Nowak, Pawel ^a   Witko, Malgorzata ^a   Heider, Johann ^b  

^a INSTITUTE OF CATALYSIS AND SURFACE CHEMISTRY   (Poland)

^b DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMICAL REACTORS; ETHYLBENZENE DEHYDROGENASE (EBDH); QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP (QSAR);

ETHYLBENZENE; HYDROXYLATION; OXIDATION; OXYGEN; STRUCTURE (COMPOSITION);

HYDROCARBONS;

1 PHENYLETHANOL; BACTERIAL ENZYME; BORIC ACID; ETHYLBENZENE; ETHYLBENZENE DEHYDROGENASE; FERROUS ION; HEMOPROTEIN; HYDROCARBON; IRON SULFUR PROTEIN; MOLYBDENUM; OXIDOREDUCTASE; OXYGEN; UNCLASSIFIED DRUG;

AROMATOLEUM AROMATICUM; ARTICLE; AZOARCUS; CHEMICAL STRESS; DENITRIFYING BACTERIUM; ELECTROCHEMICAL ANALYSIS; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME MECHANISM; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM CHEMISTRY; STEREOSPECIFICITY;

AZOARCUS; CATALYSIS; CHROMATOGRAPHY, LIQUID; ENZYME INHIBITORS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROXYLATION; KINETICS; MODELS, CHEMICAL; MODELS, THEORETICAL; MOLECULAR WEIGHT; OXIDOREDUCTASES; OXYGEN; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TANDEM MASS SPECTROMETRY;

AZOARCUS SP.; BACTERIA (MICROORGANISMS);

EID: 34250899139     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi700633c     Document Type: Article

References (28)

1. Hille, R. (1996) The mononuclear molybdenum enzymes, Chem. Rev. 96, 2757-2816.
2. Johnson, H. A., Pelletier, D. A., and Spormann, A. M. (2001) Isolation and characterization of anaerobic ethylbenzene dehydrogenase, a novel Mo-Fe-S enzyme, J. Bacteriol. 183, 4536-4542.
3. Kniemeyer, O., and Heider, J. (2001) Ethylbenzene dehydrogenase, a novel hydrocarbon-oxidizing molybdenum/iron-sulfur/heme enzyme, J. Biol. Chem. 276, 21381-21386.
4. Rabus, R., Kube, M., Beck, A., Widdel, F., and Reinhardt, R. (2002) Genes involved in the anaerobic degradation of ethylbenzene in a denitrifying bacterium, strain EbN1, Arch. Microbiol. 178, 506-516.
5. Krafft, T., Bowen, A., Theis, F., and Macy, J. M. (2000) Cloning and sequencing of the genes encoding the periplasmic-cytochrome B-containing selenate reductase of Thauera selenatis, DNA Sequence 10, 365-377.
6. McDevitt, C. A., Hugenholtz, P., Hanson, G. R., and McEwan, A. G. (2002) Molecular analysis of dimethyl sulphide dehydrogenase from Rhodovulum sulfidophilum: its place in the dimethyl sulphoxide reductase family of microbial molybdopterin-containing enzymes, Mol. Microbiol. 44, 1575-1587.
7. Lledo, B., Martinez-Espinosa, R. M., Marhuenda-Egea, F. C., and Bonete, M. J. (2004) Respiratory nitrate reductase from haloarchaeon Haloferax mediterranei: biochemical and genetic analysis, Biochim. Biophys. Acta 1674, 50-59.
8. Yoshimatsu, K., Iwasaki, T., and Fujiwara, T. (2002) Sequence and electron paramagnetic resonance analyses of nitrate reductase NarGH from a denitrifying halophilic euryarchaeote Haloarcula marismortui, FEBS Lett. 516, 145-150.
9. Kloer, D. P., Hagel, C., Heider, J., and Schulz, G. E. (2006) Crystal structure of ethylbenzene dehydrogenase from Aromatoleum aromaticum, Structure 14, 1377-1388.
10. Szaleniec, M., Jobst, B., and Heider, J. (2003) Ethylbenzene dehydrogenase: oxidation of hydrocarbons without oxygen, Ann. Pol. Chem. Soc., 240-245.
11. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. (2003) Gaussian 03, revision C.02, Gaussian, Inc., Pittsburgh, PA.
12. Hansch, C., and Alber, L. (1995) Exploring QSAR Fundamentals and Application in Chemistry and Biology, ACS Processional Reference Book, American Chemical Society, Washington, DC.
13. Fujita, T., Iwasa, J., and Hansch, C. (1964) A new substituent constant, π, derived from partition coefficients, J. Am. Chem. Soc. 86, 5175-5180.
14. Okamoto, Y., and Brown, H. C. (1957) A quantitative treatment for electrophilic reactions of aromatic derivatives, J. Org. Chem. 22, 485-494.
15. Accelrys, Inc. (2005) Cerius2 Modeling Environment, Release 4.8, Accelrys Software Inc., San Diego.
16. Stein, S. E. (2005) Mass Spectra, in NIST Chemistry WebBook (Linstrom, P. J., and Mallard, W. G., Eds.) NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg, MD, 20899 (http://webbook.nist.gov).
17. Johnstone, R. A. W., and Rose, M. E. (1996) Structure elucidation, in Mass Spectrometry for Chemist and Biochemists, 2nd ed., pp 325-395, Press Syndicate of the University of Cambridge, Cambridge.
18. Cornish-Bowden, A. (1995) Analysis of Enzyme Kinetic Data, Oxford University Press, New York.
19. Singh, P. P., Srivastava, H. K., and Pash, F. A. (2004) DFT-based QSAR study of testosterone and its derivatives, Bioorg. Med. Chem. 12, 171-177.
20. Arnett, E. M., and Ludwig, R. T. (1995) On the relevance of the Parr-Pearson principle of absolute hardness to organic chemistry, J. Am. Chem. Soc. 117, 6627-6628.
21. Szaleniec, M., Witko, M., Tadeusiewicz, R., and Goclon, J. (2006) Application of artificial neural networks and DFT-based parameters for prediction of reaction kinetics of ethylbenzene dehydrogenase, J. Comput.-Aided Mol. Des. 20, 145-157.
22. Biegert, T., Fuchs, G., and Heider, J. (1996) Evidence that oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzyl succinate from toluene and fumarate, Eur. J. Biochem. 238, 661-668.
23. Verfürth, K., Pierik, A. J., Leutwein, C., Zorn, S., and Heider, J. (2004) Substrate specificities and electron paramagnetic resonance properties of benzylsuccinate synthases in anaerobic toluene and m-xylene metabolism, Arch. Microbiol. 181, 155-162.
24. Krieger, C. J., Beller, H. R., Reinhard, M., and Spormann, A. M. (1999) Initial reactions in anaerobic oxidation of m-xylene by the denitrifying bacterium Azoarcus sp. strain T, J. Bacteriol. 181, 6403-6410.
25. Boll, M., and Fuchs, G. (1995) Benzoyl-coenzyme A reductase (dearomatizing), a key enzyme of anaerobic aromatic metabolism, Eur. J. Biochem. 234, 921-933.
26. Hansch, C., and Gao, H. (1997) Comparative QSAR: Radical reactions of benzene derivatives in chemistry and biology, Chem. Rev. 97, 2995-3059.
27. Pearson, R. G. (1987) Recent advances in the concept of hard and soft acids and bases, J. Chem. Educ. 64, 561-567.
28. Höffken, H. W., Duong, M., Friedrich, T., Breuer, M., Hauer, B., Reinhardt, R., Rabus, R., and Heider, J. (2006) Crystal structure and enzyme kinetics of the (S)-specific 1-phenylethanol dehydrogenase of the denitrifying bacterium strain EbN1, Biochemistry 45, 82-93.