Structural understanding of the glutathione-dependent reduction mechanism of glutathionyl-hydroquinone reductases

Journal of Biological Chemistry

Volumn 287, Issue 43, 2012, Pages 35838-35848

  Green, Abigail R ^a   Hayes, Robert P ^a   Xun, Luying ^a   Kangs, ChulHee ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONES; BINARY COMPLEXES; GLUTATHIONE TRANSFERASE; GLUTATHIONES; MICHAEL ADDITIONS; REDUCTION MECHANISMS; SPHINGOBIUM CHLOROPHENOLICUM;

ACTIVATION ANALYSIS; ADDITION REACTIONS; BACTERIA; ENZYMES; ESCHERICHIA COLI; FUNGI; HYDROGEN; KETONES; PEPTIDES;

PHENOLS;

CYSTEINE; GLUTATHIOLYN MENADIOL; GLUTATHIOLYN MENADIONE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; MENADIOL; MENADIONE; PROTEIN PCPF; PROTEIN YQJG; TYROSINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STRUCTURE; PRIORITY JOURNAL; REDUCTION; STRUCTURAL HOMOLOGY; STRUCTURE ACTIVITY RELATION;

ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; GLUTATHIONE; MUTATION, MISSENSE; OXIDATION-REDUCTION; OXIDOREDUCTASES; PROTEIN STRUCTURE, TERTIARY; SPHINGOMONADACEAE; VITAMIN K 3;

EID: 84867833215     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M112.395541     Document Type: Article

References (24)

1. Sheehan, D., Meade, G., Foley, V. M., and Dowd, C. (2001) Structure, function, and evolution of glutathione transferases. Implications for classification of non-mammalian members of an ancient enzyme superfamily. Biochem. J. 360, 1-16 (Pubitemid 33081943)
2. Li, J., Xia, Z., and Ding, J. (2005) Thioredoxin-like domain of human κ class glutathione transferase reveals sequence homology and structure similarity to the theta class enzyme. Protein Sci. 14, 2361-2369 (Pubitemid 41252805)
3. Dixon, D. P., Davis, B. G., and Edwards, R. (2002) Functional divergence in the glutathione transferase superfamily in plants. Identification of two classes with putative functions in redox homeostasis in Arabidopsis thaliana. J. Biol. Chem. 277, 30859-30869 (Pubitemid 34970786)
4. Xun, L., Belchik, S. M., Xun, R., Huang, Y., Zhou, H., Sanchez, E., Kang, C., and Board, P. G. (2010) S-Glutathionyl-(chloro)hydroquinone reductases. A novel class of glutathione transferases. Biochem. J. 428, 419-427
5. Meux, E., Prosper, P., Ngadin, A., Didierjean, C., Morel, M., Dumarçay, S., Lamant, T., Jacquot, J. P., Favier, F., and Gelhaye, E. (2011) Glutathione transferases of Phanerochaete chrysosporium. S-Glutathionyl-p-hydroquinone reductase belongs to a new structural class. J. Biol. Chem. 286, 9162-9173
6. Whitbread, A. K., Masoumi, A., Tetlow, N., Schmuck, E., Coggan, M., and Board, P. G. (2005) Characterization of the omega class of glutathione transferases. Methods Enzymol. 401, 78-99 (Pubitemid 43052387)
7. Lam, L. K., Zhang, Z., Board, P. G., and Xun, L. (2012) Reduction of benzoquinones to hydroquinones via spontaneous reaction with glutathione and enzymatic reaction by S-glutathionyl-hydroquinone reductases. Biochemistry 51, 5014-5021
8. Huang, Y., Xun, R., Chen, G., and Xun, L. (2008) Maintenance role of glutahionyl-hydroquinone lyase (PcpF) in pentachlorophenol degradation by Sphingobium chlorophenolicum ATCC 39723. J. Bacteriol. 190, 7595-7600
9. Belchik, S. M., and Xun, L. (2011) S-Glutathionyl-(chloro)hydroquinone reductases. A new class of glutathione transferases functioning as oxidoreductases. Drug Metab. Rev. 43, 307-316
10. Nickerson, W. J., Falcone, G., and Strauss, G. (1963) STUDIES ON QUINONE-THIOETHERS. I. MECHANISM OF FORMATION AND PROPERTIES OF THIODIONE. Biochemistry 2, 537-543
11. Otwinowski, Z., Borek, D., Majewski, W., and Minor, W. (2003) Multiparametric scaling of diffraction intensities. Acta Crystallogr A. 59, 228-234
12. Navaza, J. (2001) Implementation of molecular replacement in AMoRe. Acta Crystallogr D Biol Crystallogr. 57, 1367-1372
13. Emsley, P., Lohkamp, B., Scott, W. G., and Cowtan, K. (2010) Features and development of Coot. Acta Crystallogr. D Biol. Crystallogr. 66, 486-501
14. Adams, P. D., Afonine, P. V., Bunkóczi, G., Chen, V. B., Davis, I. W., Echols, N., Headd, J. J., Hung, L. W., Kapral, G. J., Grosse-Kunstleve, R. W., McCoy, A. J., Moriarty, N. W., Oeffner, R., Read, R. J., Richardson, D. C., Richardson, J. S., Terwilliger, T. C., and Zwart, P. H. (2010) PHENIX. A comprehensive Python-based system for macromolecular structure solution. Acta Crystallogr. D Biol. Crystallogr. 66, 213-221
15. a by isothermal titration microcalorimetry. J. Am. Chem. Soc. 126, 10508-10509
16. Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., and Olson, A. J. (2009) AutoDock4 and AutoDockTools4. Automated docking with selective receptor flexibility. J. Comput. Chem. 30, 2785-2791
17. Holm, L., and Sander, C. (1993) Protein structure comparison by alignment of distance matrices. J. Mol. Biol. 233, 123-138 (Pubitemid 23288916)
18. Altschul, S. F., Madden, T. L., Schäffer, A. A, Zhang, J., Zhang, Z., Miller, W., and Lipman, D. J. (1997) Gapped BLAST and PSI-BLAST. A new generation of protein database search programs. Nucleic Acids Res. 25, 3389-3402 (Pubitemid 27359211)
19. Board, P. G., Coggan, M., Chelvanayagam, G., Easteal, S., Jermiin, L. S., Schulte, G. K., Danley, D. E., Hoth, L. R., Griffor, M. C., Kamath, A. V., Rosner, M. H., Chrunyk, B. A., Perregaux, D. E., Gabel, C. A., Geoghegan, K. F., and Pandit, J. (2000) Identification, characterization, and crystal structure of the Omega class glutathione transferases. J. Biol. Chem. 275, 24798-24806 (Pubitemid 30626584)
20. Gilbert, H. (1995) Thiol/disulfide exchange equilibria and disulfide bond stability. Methods Enzymol. 251, 8-28
21. Nerland, D. E., and Pierce, W. M., Jr. (1990) Identification of N-acetyl-S-(2,5-dihydroxyphenyl)-L-cysteine as a urinary metabolite of benzene, phenol, and hydroquinone. Drug Metab. Dispos. 18, 958-961
22. Hill, B. A., Kleiner, H. E., Ryan, E. A., Dulik, D. M., Monks, T. J., and Lau, S. S. (1993) Identification of multi-S-substituted conjugates of hydroquinone by HPLC-coulometric electrode array analysis and mass spectroscopy. Chem. Res. Toxicol. 6, 459-469 (Pubitemid 23212514)
23. Wefers, H., and Sies, H. (1983) Hepatic low-level chemiluminescence during redox cycling of menadione and the menadione-glutathione conjugate. Relation to glutathione and NAD(P)H:quinone reductase (DT-diaphorase) activity. Arch. Biochem. Biophys. 224, 568-578
24. Brunmark, A., and Cadenas, E. (1988) Reductive addition of glutathione to p-benzoquinone, 2-hydroxy-benzoquinone, and p-benzoquinone epoxides. Effect of the hydroxy- and glutathionyl-substituents on p-benzohydroquinone autoxidation. Chem. Biol. Interact. 68, 273-298 (Pubitemid 19012625)