Geranic acid formation, an initial reaction of anaerobic monoterpene metabolism in denitrifying Alcaligenes defragrans

Applied and Environmental Microbiology

Volumn 66, Issue 7, 2000, Pages 3004-3009

  Heyen, Udo ^a   Harder, Jens ^a  

^a MAX PLANCK INSTITUTE FOR MARINE MICROBIOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

TERPENE;

ALCALIGENES; ANAEROBIC METABOLISM; ARTICLE; CATALYSIS; DENITRIFICATION; MINERALIZATION; NONHUMAN;

ALCALIGENES; ANAEROBIOSIS; CULTURE MEDIA; FATTY ACIDS; NITRATES; TERPENES;

ALCALIGENES DEFRAGRANS; NEGIBACTERIA; PROTEOBACTERIA; UNCULTURED BETA PROTEOBACTERIUM;

EID: 0033929215     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.66.7.3004-3009.2000     Document Type: Article

References (30)

1. 2 by a new type of sulfate-reducing bacterium. Arch. Microbiol. 156:4-14.
2. Butte, W. 1983. Rapid method for the determination of fatty-acid profiles from fats and oils using trimethylsulfonium hydroxide for transesteritication. J. Chromatogr. 261:142-145.
3. Coschigano, P. W., T. S. Wehrman, and L. Y. Young. 1998. Identification and analysis of genes involved in anaerobic toluene metabolism by strain T1: putative role of a glycine free radical. Appl. Environ. Microbiol. 64:1650-1656.
4. Croteau, R. 1987. Biosynthesis and catabolism of monoterpenoids. Chem. Rev. 87:929-954.
5. Cruz Costa, M. C., R. A. W. Johnstone, and J. D. Whittaker. 1996. Catalysis of gas and liquid phase ionic and radical rearrangements of α- and β-pinene by metal(IV)phosphate polymers. J. Mol. Catal. A. Chem. 104:251-259.
6. Dolfing, J., J. Zeyer, P. Binder-Eicher, and R. P. Schwarzbach. 1990. Isolation and characterization of a bacterium that mineralizes toluene in the absence of molecular oxygen. Arch. Microbiol. 154:336-341.
7. Ehrenreich, P., A. Behrends, J. Harder, and F. Widdel. 2000. Anaerobic oxidation of alkanes by newly isolated denitrifying bacteria. Arch. Microbiol. 173:58-64.
8. Erman, W. F. 1985. Chemistry of the monoterpenes, an encyclopedic handbook, part A. Marcel Dekker, Inc., New York, N.Y.
9. Fichan, I., C. Larroche, and J. B. Gros. 1999. Water solubility, vapor pressure, and activity coefficients of terpenes and terpenoids. J. Chem. Eng. Data 44:56-62.
10. Foß, S., and J. Harder. 1997. Microbial transformation of a tertiary allylalchol: regioselective isomerisation of linalool to geraniol without nerol formation. FEMS Microbiol. Lett. 149:71-75.
11. Foß, S., and J. Harder. 1998. Thauera linaloolentis sp. nov. and Thauera terpenica sp. nov., isolated on oxygen-containing monoterpenes (linalool, menthol and eucalyptol) and nitrate. Syst. Appl. Microbiol. 21:365-373.
12. Foß, S., U. Heyen, and J. Harder. 1998. Alcaligenes defragrans sp. nov., description of four strains isolated on alkenoic monoterpenes ((+)-menthene, α-pinene, 2-carene and α-phellandrene) and nitrate. Syst. Appl. Microbiol. 21:237-244.
13. Fuchs, G. 1999. Novel reactions and catalytic mechanisms in anaerobic microorganisms. FEMS Microbiol. Rev. 22:339-340.
14. Gibbs, R. A. 1998. Prenyl transfer and the enzymes of terpenoid and steroid biosynthesis, p. 31-118. In M. Sinnott (ed.), Comprehensive biological catalysis: a mechanistic reference, vol. 1. Academic Press, London, United Kingdom.
15. Gilewicz, M., G. Monpert, M. Acquaviva, G. Mille, and J. C. Bertrand. 1991. Anaerobic oxidation of l-n-heptadecene by a marine denitrifying bacterium Appl. Microbiol. Biotechnol. 36:252-256.
16. Harder, J., and C. Probian. 1995. Microbial degradation of monoterpenes in the absence of molecular oxygen. Appl. Environ. Microbiol. 61:3804-3808.
17. Harder, J., and C. Probian. 1997. Anaerobic mineralisation of cholesterol by a novel type of dentrifying bacterium. Arch. Microbiol. 167:269-274.
18. Heider, J., A. M. Spormann, H. R. Beller, and F. Widdel. 1999. Anaerobic bacterial metabolism of hydrocarbons. FEMS Microbiol. Rev. 22:459-473.
19. Heyen, U., and J. Harder. 1998. Cometabolic isoterpinolene formation from isolimonene by denitrifying Alcaligenes defragram. FEMS Microbiol. Lett. 169:67-71.
20. Iurescia, S., A. M. Marconi, D. Tofani, A. Gambacorta, A. Paternò, C. Devirgiliis, and M. J. van der Werf. 1999. Identification and sequencing of β-myrcene catabolism genes from Pseudomonas sp. strain M1. Appl. Environ. Microbiol. 65:2871-2876.
21. Leuthner, B., C. Leutwein, H. Schulz, P. Hörth, W. Haehnel, E. Schlitz, H. Schägger, and J. Heider. 1998. Biochemical and genetic characterization of benzylsuccinate synthase from Thauera aromatica: a new glycyl radical enzyme catalysing the first step in anaerobic toluene metabolism. Mol. Microbiol. 28:615-628.
22. Lovley, D. R., M. J. Baedecker, D. J. Lonergan, I. M. Cozzarelli, E. J. P. Phillips, and D. I. Siegel. 1989. Oxidation of aromatic contaminants coupled to microbial iron reduction. Nature 539:297-300.
23. Macy, J. M., J. E. Snellen, and R. E. Hungate. 1972. Use of syringe methods for anaerobiosis. Am. J. Clin. Nutr. 25:1318-1323.
24. Narushima, H., T. Omori, and Y. Minoda. 1982. Microbial oxidation of beta-myrcene, p. 525-531. In C. Verina and K. Singh (ed.), Advances in biotechnology, vol. 3. Pergamon Press, Oxford, England.
25. Rueter, P., R. Rabus, H. Wilkes, F. Aeckersberg, F. A. Rainey, H. W. Jannasch, and F. Widdel. 1994. Anaerobic oxidation of hydrocarbons in crude oil by new types of sulphate-reducing bacteria. Nature 372:455-458.
26. So, C. M., and L. Y. Young. 1999. Isolation and characterization of a sulfate-reducing bacterium that anaerobically degrades alkanes. Appl. Environ. Microbiol. 65:2969-2976.
27. Trudgill, P. W. 1994. Microbial metabolism and transformation of selected monoterpenes, p. 33-61. In C. Ratledge (ed.), Biochemistry of microbial degradation. Kluwer Academic Publishers, Dordrecht, The Netherlands.
28. van der Werf, M. J., H. J. Swarts, and J. A. M. de Bont. 1999. Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene. Appl. Environ. Microbiol. 65:2092-2102.
29. Widdel, F., and F. Bak. 1992. Gram-negative mesophilic sulfate-reducing bacteria, p. 3352-3378. In A. Balows, H. G. Trüper, M. Dworkin, W. Harder, and K. H. Schleifer (ed.), The prokaryotes, 2nd ed. Springer, Berlin, Germany.
30. Yamazaki, Y., Y. Hayashi, N. Hori, and Y. Mikami. 1988. Microbial conversion of β-myrcene. Agric. Biol. Chem. 52:2921-2922.