Metabolism and cometabolism of cyclic ethers by a filamentous fungus, a Graphium sp.

Applied and Environmental Microbiology

Volumn 75, Issue 17, 2009, Pages 5514-5522

  Skinner, Kristin ^a   Cuiffetti, Lynda ^a   Hyman, Michael ^b  

^a OREGON STATE UNIVERSITY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DEHYDROGENASE; BUTYROLACTONES; COMETABOLISM; CYCLIC ETHER; DIETHYL ETHERS; FILAMENTOUS FUNGI; GASOLINE OXYGENATES; HEMIACETALS; LAG PHASE; METHYL FORMATE; METHYL TERT BUTYL ETHER; N-ALKANES; N-ALKENES; OXIDIZING ACTIVITY; OXYGENASES; TERMINAL DIOLS; TETRAHYDROFURANS; TETRAHYDROPYRAN;

ACETYLENE; ETHERS; METABOLISM; METABOLITES; METHANOL; OLEFINS; ORGANIC COMPOUNDS; OXIDATION; PROPANE;

PARAFFINS;

ALCOHOL DEHYDROGENASE; ALKANE; CYCLOHEXANE; DIOXANE; ETHER; ETHER DERIVATIVE; FORMALDEHYDE; GAMMA BUTYROLACTONE; LACTONE; METHANOL; PROPANE; TERT BUTYL METHYL ETHER; TETRAHYDROPYRAN DERIVATIVE; UNSPECIFIC MONOOXYGENASE;

ALKANE; BIODEGRADATION; ENZYME ACTIVITY; FUNGUS; FURAN; GROWTH RATE; METABOLISM; MICROBIAL ACTIVITY; MTBE; OXIDATION;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FUNGAL METABOLISM; FUNGAL STRAIN; FUNGUS; FUNGUS GROWTH; GRAPHIUM; MYCELIAL GROWTH; NONHUMAN; OXIDATION;

4-BUTYROLACTONE; ASCOMYCOTA; DIOXANES; ETHERS, CYCLIC; FORMALDEHYDE; FORMIC ACID ESTERS; FURANS; METABOLIC NETWORKS AND PATHWAYS; METHANOL; MODELS, BIOLOGICAL; MYCELIUM; PROPANE;

FUNGI;

EID: 69549137027     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.00078-09     Document Type: Article

References (51)

1. April, T. M., S. P. Abbott, J. M. Foght, and R. S. Currah. 1998. Degradation of hydrocarbons in crude oil by the ascomycete Pseudoallescheria boydii (Microascaceae). Can. J. Microbiol. 44:270-278.
2. Bernhardt, D., and H. Diekmann. 1991. Degradation of dioxane, tetrahydrofuran and other cyclic ethers by an environmental Rhodococcus strain. Appl. Microbiol. Biotechnol. 36:120-123.
3. Bock, C., R. M. Kroppenstedt, and H. Diekmann. 1996. Degradation and bioconversion of aliphatic and aromatic hydrocarbons by Rhodococcus ruber 219. Appl. Microbiol. Biotechnol. 45:408-410.
4. Burback, B. L., and J. J. Perry. 1993. Biodegradation and biotransformation of groundwater pollutant mixtures by Mycobacterium vaccae. Appl. Environ. Microbiol. 59:1025-1029.
5. Carlier, A., R. Chevrot, Y. Dessaux, and D. Faure. 2004. The assimilation of gamma butyrolactone in Agrobacterium tumefaciens C58 interferes with the accumulation of the N-acyl-homoserine lactone signal. Mol. Plant-Microbe Interact. 17:951-957.
6. Chai, Y., C. S. Tsai, H. Cho, and S. C. Winans. 2007. Reconstitution of the biochemical activities of the AttJ repressor and the AttK, AttL, and AttM catabolic enzymes of Agrobacterium tumefaciens. J. Bacteriol. 189:3674-3679. (Pubitemid 46668836)
7. Cherot, R., R. Rosen, E. Haudecoeur, A. Cirou, B. J. Shelp, E. Ron, and D. Faure. 2006. GABA controls the level of quorum-sensing signal in Agrobacterium tumefaciens. Proc. Natl. Acad. Sci. USA 103:7460-7464.
8. Ciolino, L. A., M. Z. Mesmer, R. D. Satzger, A. C. Machal, B. S. Heather, A. McCauley, and A. S. Mohrhaus. 2001. The chemical interconversion of GHB and GBL: forensic issues and implications. J. Forensic Sci. 46:1315-1323.
9. Curragh, H., O. Flynn, M. J. Larkin, T. M. Stafford, J. T. Hamilton, and D. B. Harper. 1994. Haloalkane degradation and assimilation by Rhodococcus rhodochrous NCIMB 13064. Microbiology 140:1433-1442.
10. Curry, S., L. M. Ciuffetti, and M. R. Hyman. 1996. Inhibition of growth of Graphium sp. on gaseous n-alkanes by gaseous n-alkynes and n-alkenes. Appl. Environ. Microbiol. 62:2198-2200. (Pubitemid 26169026)
11. Davies, J. S., J. E. Zajic, and A. Wellman. 1974. Fungal oxidation of gaseous alkanes. Dev. Ind. Microbiol. 15:256-262.
12. Daye, K. J., J. C. Groff, A. C. Kirpekar, and R. Mazumder. 2003. High efficiency degradation of tetrahydrofuran (THF) using a membrane bioreactor: identification of THF-degrading cultures of Pseudonocardia sp. strain M1 and Rhodococcus ruber isolate M2. J. Ind. Microbiol. Biotechnol. 30:705-714.
13. Hardison, L. K., S. S. Curry, L. M. Ciuffetti, and M. R. Hyman. 1997. Metabolism of diethyl ether and cometabolism of methyl tert-butyl ether by a filamentous fungus, Graphium sp. Appl. Environ. Microbiol. 63:3059-3067. (Pubitemid 27337794)
14. Hurd, C. D., and W. H. Saunders. 1952. Ring chain tautomerism of hydroxy aldehydes. J. Am. Chem. Soc. 74:5324-5329.
15. Iida, T., T. Sumita, A. Ohta, and M. Takagi. 2000. The cytochrome P450ALK multigene family of an n-alkane-assimilating yeast Yarrowia lipolytica: cloning and characterization of genes coding for new CYP52 family members. Yeast 16:1077-1087.
16. Jones, J. B., and K. P. Lok. 1979. Enzymes in organic synthesis. 14. Stereo-selective horse liver alcohol dehydrogenase catalyzed oxidations of diols containing a prochiral centre and of related hemiacetals. Can. J. Chem. 57:1025-1032.
17. Kämpfer, P., U. Kohlweyer, B. Thiemer, and J. R. Andreesen. 2006. Pseudonocardia tetrahydrofuranoxydans sp. nov. Int. J. Syst. Evol. Microbiol. 56:1535-1538.
18. Kang, J. W., and W. L. Hergenrother. December 1978. Preparation of 2,3-dihydrofuran. U.S. patent 4,129,579.
19. Kendal, L. P., and A. N. Ramanathan. 1952. Liver alcohol dehydrogenase and ester formation. Biochem. J. 52:430-438.
20. Kim, Y.-M., J.-R. Jeon, K. Murugesan, E.-J. Kim, and Y.-S. Chang. 2009. Biodegradation of 1,4-dioxane and transformation of related cyclic compounds by a newly isolated Mycobacterium sp. PH-06. Biodegradation 20:511-519.
21. Kohlweyer, U., B. Thiemer, T. Schrader, and J. R. Andreesen. 2000. Tetrahydrofuran degradation by a newly isolated culture of Pseudonocardia sp. strain K1. FEMS Microbiol. Lett. 186:301-306.
22. Kusano, M., Y. Sakai, N. Kato, H. Yoshimoto, H. Sone, and Y. Tani. 1998. Hemiacetal dehydrogenase activity in alcohol dehydrogenases in Saccharomyces cerevisiae. Biosci. Biotechnol. Biochem. 62:1956-1961.
23. Lawson, A. P., and J. A. Klang. October 1993. Process for preparation of 2-oxytetrahydrofurans. U.S. patent 5,254,702.
24. Liu, C. Y., G. E. Speitel, Jr., and G. Georgiou. 2001. Kinetics of methyl t-butyl ether cometabolism at low concentrations by pure cultures of butane-degrading bacteria. Appl. Environ. Microbiol. 67:2197-2201.
25. Lütke-Eversloh, T., and A. Steinbüchel. 1999. Biochemical and molecular characterization of a succinate semialdehyde dehydrogenase involved in the catabolism of 4-hydroxybutyric acid in Ralstonia eutropha. FEMS Microbiol. Lett. 181:63-71. (Pubitemid 29516604)
26. Mackay, D. M., and W. Ying. 1981. Critical review of Henry's law constants for chemicals of environmental interest. J. Phys. Chem. 10:1175-1195.
27. Mahendra, S., and L. Alvarez-Cohen. 2005. Pseudonocardia dioxanivorans sp. nov., a novel actinomycete that grows on 1,4-dioxane. Int. J. Syst. Evol. Microbiol. 55:593-598.
28. Mahendra, S., and L. Alvarez-Cohen. 2006. Kinetics of 1,4-dioxane biodegradation by monooxygenase-expressing bacteria. Environ. Sci. Technol. 40:5435-5442.
29. Mohr, T. K. G. 2001. Solvent stabilizers white paper. Santa Clara Valley Water District, San Jose, CA. http://www.valleywater.org/Water/Water-Quality/ Protecting-your-water/-Solvents/-PDFs/SolventStabilizers.pdf.
30. Moreno-Horn, M., L.-A. Garbe, R. Tressi, and H. Görisch. 2005. Transient accumulation of γ-butyrolactone during degradation of bis(4-chloro-n-butyl) ether by diethylether-grown Rhodococcus sp. strain DTB. Appl. Microbiol. Biotechnol. 69:335-340. (Pubitemid 43014452)
31. +-dependent dehydrogenation of hemiacetal: production of methyl formate by cells of methylotrophic yeasts. Biosci. Biotechnol. Biochem. 61:1391-1393.
32. Murdanoto, A. P., Y. Sakai, T. Konishi, F. Tasuda, Y. Tani, and N. Kato. 1997. Purification and properties of methyl formate synthase, a mitochondrial alcohol dehydrogenase, participating in formaldehyde oxidation in methylotrophic yeasts. Appl. Environ. Microbiol. 63:1715-1720.
33. Nakamiya, K., S. Hashimoto, H. Ito, J. S. Edmonds, and M. Morita. 2005. Degradation of 1,4-dioxane and cyclic ethers by an isolated fungus. Appl. Environ. Microbiol. 71:1254-1258.
34. Ohkuma, M., S.-I. Muraoka, T. Tanimoto, M. Fujii, A. Ohta, and M. Takagi. 1995. CYP52 (cytochrome P450alk) multigene family in Candida maltosa: identification and characterization of eight members. DNA Cell Biol. 14:163-173.
35. Parales, R. E., J. E. Adamus, N. White, and H. D. May. 1994. Degradation of 1,4-dioxane by an actinomycete in pure culture. Appl. Environ. Microbiol. 60:4527-4530.
36. Patt, T. E., and H. M. Abede. March 1993. Microbial degradation of chemical pollutants. U.S. patent 5,399,495.
37. Sakai, Y., A. P. Murdanoto, L. Sembiring, Y. Tani, and N. Kato. 1995. A novel formaldehyde oxidation pathway in methylotrophic yeasts: methyl formate as a possible intermediate. FEMS Microbiol. Lett. 127:229-234.
38. Schiller, J. G., and A. E. Chung. 1970. The metabolism of cyclopropanecarboxylic acid. J. Biol. Chem. 245:5857-5864.
39. Skinner, K. M., A. Martinez-Prado, M. R. Hyman, K. J. Williamson, and L. M. Ciuffetti. 2008. Pathway, inhibition and regulation of methyl tertiary butyl ether oxidation in a filamentous fungus, Graphium sp. Appl. Microbiol. Biotechnol. 77:1359-1365.
40. Skinner, K. M. 2008. Ph.D. dissertation. Oregon State University, Corvallis. http://ir.library.oregonstate.edu/dspace/bitstream/1957/4952/1/KM- Skinner-Dissertation.pdf.
41. Smith, C. A., K. T. O'Reilly, and M. R. Hyman. 2003. Characterization of the initial reactions during the cometabolic oxidation of methyl tert-butyl ether by propane-grown Mycobacterium vaccae JOB5. Appl. Environ. Microbiol. 69:796-804.
42. Thiemer, B., J. R. Andreesen, and T. Schrader. 2003. Cloning and characterization of a gene cluster involved in tetrahydrofuran degradation in Pseudonocardia sp. strain K1. Arch. Microbiol. 179:266-277.
43. U.S. Environmental Protection Agency. January 2006, revision date. 1990 high production volume challenge program chemical list. Office of Prevention, Pesticides, and Toxic Substances, U.S. Environmental Protection Agency, Washington, DC.
44. U.S. Environmental Protection Agency. 1995. OPPT-chemical fact sheets. 1,4-Dioxane fact sheet. EPA-749-F-95-0102. Office of Pollution Prevention and Toxic Substances, U.S. Environmental Protection Agency, Washington, DC.
45. Vainberg, S., K. McClay, H. Masuda, D. Root, C. Condee, G. J. Zylstra, and R. J. Steffan. 2006. Biodegradation of ether pollutants by Pseudonocardia sp. strain ENV478. Appl. Environ. Microbiol. 72:5218-5224.
46. Vatsyayan, P., A. K. Kumar, P. Goswami, and P. Goswami. 2008. Broad substrate cytochrome P450 monooxygenase activity in the cells of Aspergillus terreus MTCC 6324. Bioresour. Technol. 99:68-75.
47. Yurimoto, H., B. Lee, F. Yasuda, Y. Sakai, and N. Kato. 2004. Alcohol dehydrogenases that catalyze methyl formate synthesis participate in formaldehyde detoxification in the methylotrophic yeast Candida boidinii. Yeast 21:341-350. (Pubitemid 38425532)
48. Zajic, J. E., B. Volesky, and A. Wellman. 1969. Growth of Graphium sp. on natural gas. Can. J. Microbiol. 15:1231-1236.
49. Zenker, M. J., R. C. Borden, and M. A. Barlaz. 2003. Occurrence and treatment of 1,4-dioxane in aqueous environments. Environ. Eng. Sci. 20:423-432.
50. Zhang, X., J. H. Xu, Y. Xu, and J. Pan. 2007. Isolation and properties of a levolactonase from Fusarium proliferatum ECU2002: a robust biocatalyst for production of chiral lactones. Appl. Microbiol. Biotechnol. 75:1087-1094.
51. Zimmer, T., M. Ohkuma, A. Ohta, M. Takagi, and W.-H. Schunck. 1996. The CYP52 multigene family of Candida maltosa encodes functionally diverse n-alkane-inducible cytochromes P450. Biochem. Biophys. Res. Commun. 224:784-789.