Iron(II)-dependent dioxygenase and N-formylamide deformylase catalyze the reactions from 5-hydroxy-2-pyridone to maleamate

Scientific Reports

Volumn 3, Issue , 2013, Pages

  Yao, Yuxiang ^a   Tang, Hongzhi ^a   Ren, Huixue ^b   Yu, Hao ^a   Wang, Lijuan ^a   Zhang, Wei ^a   Behrman, Edward J ^c   Xu, Ping ^a  

^a Shanghai Jiao Tong University   (China)

^b Shandong Jian Zhu University   (China)

^c OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84888143939     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep03235     Document Type: Article

References (34)

1. Padoley, K.V.,Mudliar, S. N. & Pandey, R. A. Heterocyclic nitrogenous pollutants in the environment and their treatment options-an overview. Bioresource Technol. 99, 4029-4043 (2008) (Pubitemid 351380786)
2. Wang, S. N. et al. Biodegradation and detoxification of nicotine in tobacco solid waste by a Pseudomonas sp. Biotechnol. Lett. 26, 1493-1496 (2004) (Pubitemid 41440524)
3. Sims, G. K., O'Loughlin, E. J. & Crawford, R. L. Degradation of pyridines in the environment. Crit. Rev. Environ. Control 19, 309-340 (1989)
4. Richards, D. J. & Shieh,W. K. Biological fate of organic priority pollutants in the aquatic environment. Water Res. 20, 1077-1090 (1986)
5. Rogers, J. E., Riley, R. G., Li, S. W., O'Malley, M. L. & Thomas, B. L. Microbial transformation of alkylpyridines in groundwater. Water Air Soil Pollut. 24, 443-454 (1985) (Pubitemid 15138181)
6. Kuhn, E. P. & Suflita, J. M. Microbial degradation of nitrogen, oxygen and sulfur heterocyclic compounds under anaerobic conditions: studies with aquifer samples. Environ. Toxicol. Chem. 8, 1149-1158 (1989)
7. Kaiser, J. P., Feng, Y. & Bollag, J. M. Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions. Microbiol. Rev. 60, 483-498 (1996) (Pubitemid 26303475)
8. Orpin, C.G., Knight, M. & Evans, W. C. The bacterial oxidation of picolinamide, a photolytic product of diquat. Biochem. J. 127, 819-831 (1972)
9. Shukla, O. P. & Kaul, S. M. Microbiological transformation of pyridine N-oxide and pyridine by Nocardia sp. Can. J. Microbiol. 32, 330-341 (1986) (Pubitemid 16055426)
10. Tang, H. Z. et al. Genomic analysis of Pseudomonas putida: genes in a genome island are crucial for nicotine degradation. Sci. Rep. 2, 377, doi:10.1038/srep00377 (2012)
11. Tang, H. Z. et al. Systematic unraveling of the unsolved pathway of nicotine degradation in Pseudomonas. PLoS Genet. 9, e1003923, doi:10.1371/ journal.pgen.1003923 (2013)
12. Cain, R. B., Houghton, C. & Wright, K. A. Microbial metabolism of the pyridine ring: metabolism of 2-and 3-hydroxypyridines by the maleamate pathway in Achromobacter sp. Biochem. J. 140, 293-300 (1974)
13. Jimenez, J. I. et al. Deciphering the genetic determinants for aerobic nicotinic acid degradation: the nic cluster from Pseudomonas putida KT2440. Proc. Natl. Acad. Sci. USA 105, 11329-11334 (2008)
14. Kim, S. G. & Novak, R. F. Role of P450IIE1 in the metabolism of 3- hydroxypyridine, a constituent of tobacco smoke: redox cycling and DNA strand scission by the metabolite 2,5-dihydroxypyridine. Cancer Res. 50, 5333-5339 (1990) (Pubitemid 20302984)
15. Behrman, E. J. & Stanier, R. Y. The bacterial oxidation of nicotinic acid. J. Biol. Chem. 228, 923-945 (1957)
16. Stanier, R. Y., Palleroni, N. J. & Doudoroff, M. The aerobic Pseudomonads: a taxonomic study. J. Gen. Microbiol. 43, 159-271 (1966)
17. Gauthier, J. J. & Rittenberg, S. C. The metabolism of nicotinic acid. I. purification and properties of 2,5-dihydroxypyridine oxygenase from Pseudomonas putida N- 9. J. Biol. Chem. 246, 3737-3742 (1971)
18. Gauthier, J. J. & Rittenberg, S. C. The metabolism of nicotinic acid. II. 2,5- dihydroxypyridine oxidation, product formation, and oxygen 18 incorporation. J. Biol. Chem. 246, 3743-3748 (1971)
19. Behrman, E. J. The bacterial oxidation of nicotinic acid. N-formylmaleamic and N-formylfumaramic acids. Arch. Microbiol. 110, 87-90 (1976)
20. Behrman, E. J. N-formylmaleamic acid: an intermediate in nicotinic acid metabolism. Proc. Natl. Acad. Sci. USA 105, E88 (2008)
21. Jimenez, J. I. et al. Reply to Behrman:"N-Formylmaleamic acid: an intermediate in nicotinic acid metabolism". Proc. Natl. Acad. Sci. USA 105, E89 (2008)
22. Behrman, E. J. & Hillenbrand, E. L. Synthesis ofN-formylmaleamic acid and some related N-formylamides. J. Chem. Res. 170-172 (2008)
23. Koehntop, K. D., Emerson, J. P. & Que, L. The 2-His-1-carboxylate facial triad: a versatile platform for dioxygen activation by mononuclear non-heme iron(II) enzymes. J. Biol. Inorg. Chem. 10, 87-93 (2005) (Pubitemid 40569003)
24. Odintsov, S. G., Sabala, I., Bourenkov, G., Rybin, V. & Bochtler, M. Staphylococcus aureus aminopeptidase S is a founding member of a new peptidase clan. J. Biol. Chem. 280, 27792-27799 (2005) (Pubitemid 41076894)
25. Holmquist, M. Alpha/beta-hydrolase fold enzymes: structures, functions and mechanisms. Curr. Protein Pept. Sci. 1, 209-235 (2000)
26. Jimenez, J. I., Acebron, I., Garc?a, J. L., D?az, E. & Mancheno, J. M. A preliminary crystallographic study of recombinant NicX, an Fe(21)-dependent 2,5- dihydroxypyridine dioxygenase from Pseudomonas putida KT2440. Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 66, 549-553 (2010)
27. Sambrook, J. & Russell, D. W. Molecular cloning: a laboratory manual. 3rd edn, Vol. 1, (Cold Spring Harbor Laboratory press, 2001)
28. Hattori, A. et al. Characterization of recombinant human adipocyte-derived leucine aminopeptidase expressed in Chinese hamster ovary cells. J. Biochem. 128, 755-762 (2000)
29. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254 (1976)
30. Southern, E. M. Detection of specific sequences among DNA fragments separated by gel electrophoresis. J. Mol. Biol. 98, 503-517 (1975)
31. Tang, H. Z. et al. A novel NADH-dependent and FAD-containing hydroxylase is crucial for nicotine degradation by Pseudomonas putida. J. Biol. Chem. 286, 39179-39187 (2011)
32. Bryson, K. et al. Protein structure prediction servers at University College London. Nucleic Acids Res. 33, W36-38 (2005) (Pubitemid 44529876)
33. Han, S., Eltis, L. D., Timmis, K. N., Muchmore, S. W. & Bolin, J. T. Crystal structure of the biphenyl-cleaving extradiol dioxygenase from a PCB-degrading pseudomonad. Science 270, 976-980 (1995)
34. Nardini, M. et al. The x-ray structure of epoxide hydrolase from Agrobacterium radiobacter AD1. An enzyme to detoxify harmful epoxides. J. Biol. Chem. 274, 14579-14586 (1999).