Morpholine degradation pathway of Mycobacterium aurum MO1: Direct evidence of intermediates by in situ 1H nuclear magnetic resonance

Applied and Environmental Microbiology

Volumn 64, Issue 1, 1998, Pages 153-158

  Combourieu, B ^a   Besse, P ^a   Sancelme, M ^a   Veschambre, H ^a   Delort, A M ^a   Poupin, P ^b   Truffaut, N ^b  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b UNIVERSITÉ DE TECHNOLOGIE DE COMPIÈGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MORPHOLINE;

ARTICLE; BACTERIAL METABOLISM; BIODEGRADATION; MYCOBACTERIUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM AURUM;

EID: 0031975091     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.64.1.153-158.1998     Document Type: Article

References (33)

1. Brown, V. R., J. S. Knapp, and J. Heritage. 1990. Instability of the morpholine degradative phenotype in mycobacteria isolated from activated sludge. J. Appl. Bacteriol. 69:54-62.
2. Carlsen, P. H. J., T. Katsuki, V. S. Martin, and K. B. Sharpless. 1981. A greatly improved procedure for rhutenium tetraoxide catalyzed oxidations of organic compounds. J. Org. Chem. 46:3936-3938.
3. Cech, J. S., P. Hartman, M. Slosarek, and J. Chudoba. 1988. Isolation and identification of a morpholine-degrading bacterium. Appl. Environ. Microbiol. 54:619-621.
4. Dean-Ross, D., and C. E. Cerniglia. 1996. Degradation of pyrene by Mycobacterium flavescens. Appl. Microbiol. Biotechnol. 46:307-312.
5. Dmitrenko, G. N., V. M. Udod, and P. I. Gvozdyak. 1985. Destruction of morpholine by fixed bacteria. Khim. Teknol. Vody 7:97-99.
6. Emtiazi, G., and J. S. Knapp. 1994. The biodegradation of piperazine and structurally-related linear and cyclic amines. Biodegradation 5:83-92.
7. Gaines, G. L. III, L. Smith, and E. L. Neidle. 1996. Novel nuclear magnetic resonance spectroscopy methods demonstrate preferential carbon source utilization by Acinetobacter calcoaceticus. J. Bacteriol. 178:6833-6841.
8. 13C NMR investigation. Eur. J. Biochem. 207:155-162.
9. German Chemical Society. 1993. Advisory Committee on Existing Chemicals of Environmental Relevance, Morpholine BUA report 56, December 1990. S. Hirzel, Stuttgart, Germany.
10. Guerin, W. F., and G. E. Jones. 1988. Mineralization of phenanthrene by a Mvcobacterium sp. Appl. Environ. Microbiol. 54:937-944.
11. Häggblom, M. M., L. J. Nohynek, and M. S. Salkinoja-Salonen. 1988. Degradation and O methylation of chlorinated phenolic compounds by Rhodococcus and Mycobacterium strains. Appl. Environ. Microbiol. 54:3043-3052.
12. Hartmans, S., and J. A. M. de Bont. 1992. Aerobic vinyl chloride metabolism in Mycobacterium aurum L1. Appl. Environ. Microbiol. 58:1220-1226.
13. Heitkamp, M. A., and C. E. Cerniglia. 1989. Polycyclic aromatic hydrocarbon degradation by a Mycobacterium sp. in microcosms containing sediment and water from a pristine ecosystem. Appl. Environ. Microbiol. 55:1968-1973.
14. Kleespies, M. R. M., F. A. Kroppenstedt, L. E. Rainey, L. E. Webb, and E. Stackebrandt. 1996. Mycobacterium hodleri sp. nov., a new member of the fast-growing mycobacteria capable of degrading polycyclic aromatic hydrocarbons. Int. J. Syst. Bacteriol. 46:683-687.
15. Knapp, J. S., A. G. Callely, and J. Mainprize. 1982. The microbial degradation of morpholine. J. Appl. Bacteriol. 52:5-13.
16. Knapp, J. S., and V. R. Brown. 1988. Morpholine biodegradation. Int. Biodeterior. 24:299-306.
17. Knapp, J. S., and A. J. Whytell. 1990. The biodegradation of morpholine in river water and activated sludge. Environ. Pollut. 68:67-79.
18. Kretzer, A., and J. R. Andreesen. 1991. A new pathway for isonicotinate degradation by Mycobacterium sp. INA1. J. Gen. Microbiol. 137:1073-1080.
19. Mazure, N., and N. Truffaut. 1994. Degradation of morpholine by Mycobacterium aurum MO1. Can. J. Microbiol. 40:761-765.
20. 1H NMR analysis of amniotic fluid. J. Pharm. Biomed. Analysis 11:629-632.
21. Mirwish, S. S., S. Salmasi, S. M. Cohen, K. Patil, and E. Mahboubi. 1983. Liver and forestomach tumors, and other forestomach lesions in rats treated with morpholine and sodium nitrite with and without sodium ascorbate. JNCI 71:81-85.
22. Mjos, K. 1978. Cyclic amines, p. 295-308. In Kirk-Othmer encyclopaedia of chemical technology, 3rd ed. vol. 2. Wiley Interscience, New York, N.Y.
23. Naughton, D. P., R. Haywood, O. R. Blake, S. Edmunds, G. E. Hawkes, and M. Grootveld. 1993. A comparative evaluation of the metabolic profiles of normal and inflammatory knee-joint synovial fluids by high resolution proton NMR spectroscopy. FEBS Lett. 332:221-225.
24. Poupin, P., N. Truffaut, B. Combourieu, P. Besse, M. Sancelme, H. Veschambre, and A. M. Delort. 1998. Degradation of morpholine by an environmental Mycobacterium strain involves a cytochrome P-450. Appl. Environ. Microbiol. 64:159-165.
25. Sauto, S., H. Nakajima, M. Inaba, and T. Moriwake. 1989. One-pot transformation of azido-group to N-(t-butoxycarbonyl)amino group. Tetrahedron Lett. 30:837-838.
26. Stahl, G. L., R. Walter, and C. W. Smith. 1978. General procedure for the synthesis of mono-N-acylated 1,6-diaminohexanes. J. Org. Chem. 43:2285-2287.
27. Suzuki, S., and T. Mitsuoka. 1984. N-nitrosamine formation by intestinal bacteria. I.A.R.C. Sci. Publ. 57:275-282.
28. Swain, A., K. V. Waterhouse, W. A. Venables, A. G. Callely, and S. E. Lowe. 1991. Biochemical studies of morpholine catabolism by an environmental mycobacterium. Appl. Microbiol. Biotechnol. 35:110-114.
29. Tiehm, A., and C. Fritzsche. 1995. Utilisation of solubilized and crystalline mixtures of polycyclic aromatic hydrocarbons by a Mycobacterium sp. Appl. Microbiol. Biotechnol. 42:964-968.
30. 1H NMR spectroscopy. Eur. J. Biochem. 228:727-731.
31. 13C nuclear magnetic resonance to elucidate the unexpected biosynthesis of erythritol by Leuconostoc oenos. Appl. Environ. Microbiol. 58: 2271-2279.
32. Vieles, P., and J. Séguin. 1953. Synthèses de morpholones-3 et d'oxazolidone-2. Bull. Soc. Chim. Fr. 287-289.
33. Wackett, L. P., G. A. Brusseau, S. R. Householder, and R. S. Hanson. 1989. Survey of microbial oxygenases: trichloroethylene degradation by propane-oxidizing bacteria. Appl. Environ. Microbiol. 55:2960-2964.