1887

Abstract

The bacterium NCIMB 13064, isolated from an industrial site, could use a wide range of 1-haloalkanes as sole carbon source but apparently utilized several different mechanisms simultaneously for assimilation of substrate. Catabolism of 1-chlorobutane occurred mainly by attack at the C-1 atom by a hydrolytic dehalogenase with the formation of butanol which was metabolized via butyric acid. The detection of small amounts of γ-butyrolactone in the medium suggested that some oxygenase attack at C-4 also occurred, leading to the formation of 4-chlorobutyric acid which subsequently lactonized chemically to γ-butyrolactone. Although 1-chlorobutane-grown cells exhibited little dehalogenase activity on 1-chloroalkanes with chain lengths above C, the organism utilized such compounds as growth substrates with the release of chloride. Concomitantly, γ-butyrolactone accumulated to 1 mM in the culture medium with 1-chlorohexadecane as substrate. Traces of 4-hydroxybutyric acid were also detected. It is suggested that attack on the long-chain chloroalkane is initiated by an oxygenase at the non-halogenated end of the molecule leading to the formation of an Ω-chlorofatty acid. This is degraded by β-oxidation to 4-chlorobutyric acid which is chemically lactonized to γ-butyrolactone which is only slowly further catabolized via 4-hydroxybutyric acid and succinic acid. However, release of chloride into the medium during growth on long-chain chloroalkanes was insufficient to account for all the halogen present in the substrate. Analysis of the fatty acid composition of 1-chlorohexadecane-grown cells indicated that chlorofatty acids comprised 75% of the total fatty acid content with C, C, C and C acids predominating. Thus the incorporation of 16-chlorohexadecanoic acid, the product of oxygenase attack directly into cellular lipid represents a third route of chloroalkane assimilation. This pathway accounts at least in part for the incomplete mineralization of long-chain chloroalkane substrates. This is the first report of the coexistence of a dehalogenase and the ability to incorporate long-chain haloalkanes into the lipid fraction within a single organism and raises important questions regarding the biological treatment of haloalkane containing effluents.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-140-6-1433
1994-06-01
2021-07-30
Loading full text...

Full text loading...

/deliver/fulltext/micro/140/6/mic-140-6-1433.html?itemId=/content/journal/micro/10.1099/00221287-140-6-1433&mimeType=html&fmt=ahah

References

  1. Bagley D. M., Gossett J. M. 1990; Tetrachloroethane transformation to trichloroethene and r/r-l,2-dichloroethene by sulphate-reducing enrichment cultures. Appl Environ Microbiol 56:2511–2516
    [Google Scholar]
  2. Bernhardt D., Diekmann H. 1991; Degradation of dioxane, tetrahvdrofuran and other cyclic ethers by an environmental Rhodococcus strain. Appl Microbiol Biotechnol 36:120–123
    [Google Scholar]
  3. Bouwer E.J., McCarty P. L. 1983; Transformations of halogenated organic compounds under denitrification conditions. Appl Environ Microbiol 45:1295–1299
    [Google Scholar]
  4. Dunlap K.R., Perry J. J. 1967; Effect of substrate on the fatty acid composition of hydrocarbon utilizing microorganisms. J Bacterial 94:1919–1923
    [Google Scholar]
  5. Elfaki A. E., Dirar H. A., Collins M. A., Harper D. B. 1991; Biochemical and microbiological investigations of sigda - a Sudanese fermented food derived from sesame oilseed cake. J Sci Food. Iuric 57:351–365
    [Google Scholar]
  6. Fox A., Gilbart J., Morgan S. L. 1990; Analytical microbiology: a perspective. In Analytical Microbiology Methods. Chromatography and Mass Spectrometry pp. 1–17 Edited by Fox A., Morgen S. L. , Larsson L., Odham G. . New York: Plenum Press;
    [Google Scholar]
  7. Janssen D. B., Scheper A., Dijkhuizen L., Witholt B. 1985; Degradation of halogenated aliphatic compounds by Xanthobacter autotrophicus GJ10. Appl Environ Microbiol 49:673–677
    [Google Scholar]
  8. Janssen D. B., Jager D., Witholt B. 1987; Degradation of n- haloalkanes and a,co-dichloroalkanes by wild-type and mutants of Acinetobacter sp. strain GJ70. Appl Environ Microbiol 53:561 –566
    [Google Scholar]
  9. Janssen D. B., Gerritse J., Brackman J., Kalk C., Jager D., Witholt B. 1988a; Purification and characterization of a bacterial dehalogenase with activity toward halogenated alkanes, alcohols and ethers. Ear J Biochem 171:67–72
    [Google Scholar]
  10. Janssen D. B., Grobben G., Hoekstra R., Oldenhuis R., Witholt B. 1988b; Degradation of trans-1,2-dichloroethene by mixed and pure cultures of methanotrophic bacteria. Appl Microbiol Biotechnol 29:392–399
    [Google Scholar]
  11. Keuning S., Janssen D. B., Witholt B. 1985; Purification and characterization of a hydrolytic haloalkane dehalogenase from Xanthobacter autotrophicus GJ10. J Bacterial 163:635–639
    [Google Scholar]
  12. Kohler-Staub D, Leisinger T. 1985; Dichloromethane dehalogenase from Hyphomicrobium sp. IM2. J Bacteriol 162:676–681
    [Google Scholar]
  13. Marks T. S., Allpress J. D., Maule A. 1989; Dehalogenation of lindane by a variety of porphyrins and corrins. Appl Environ Microbiol 55:1258–1261
    [Google Scholar]
  14. Murphy G.L., Perry J. J. 1983; Incorporation of chlorinated alkanes into fatty acids of hydrocarbon-utilizing mycobacteria. J Bacteriol 156:1158–1164
    [Google Scholar]
  15. Murphy G.L., Perry J. J. 1984; Assimilation of chlorinated alkanes by hydrocarbon-utilizing fungi. J Bacteriol 160:1171–1174
    [Google Scholar]
  16. Oldenhuis R., Vink R. L. J. M., Janssen D. B., Witholt B. 1989; Degradation of chlorinated aliphatic hydrocarbons by Methylo- sinus trichosporium OB3b expressing soluble methane monooxygenase. Appl Environ Microbiol 55:2819–2826
    [Google Scholar]
  17. Rasche M. E., Hicks R. E., Hyman M. R., Arp D. J. 1990; Oxidation of monohalogenated ethanes and n-chlorinated alkanes by whole cells of Nitrosomonas europaea. J Bacteriol 172:5368– 5373
    [Google Scholar]
  18. Sallis P. J., Armfield S. J., Bull A. T., Hardman D. J. 1990; Isolation and characterization of a haloalkane halidohydrolase from Rhodococcus erythropolis Y2. J Gen Microbiol 136:115–120
    [Google Scholar]
  19. Scholtz R., Leisinger T., Suter F., Cook A. M. 1987a; Characterization of 1-chlorohexane halidohydrolase, a dehalogenase of wide substrate range from an Arthrobacter sp. J Bacteriol 169:5016–5021
    [Google Scholar]
  20. Scholtz R., Schmuckle A., Cook A. M., Leisinger T. 1987b; Degradation of eighteen 1-monohaloalkanes by Arthrobacter sp. H A1. J Gen Microbiol 133:267–274
    [Google Scholar]
  21. Scholtz R., Messi F., Leisinger T., Cook A. M. 1988; Three dehalogenases and physiological restraints in the biodegradation of haloalkanes by Arthrobacter sp. strain HA1. Appl Environ Microbiol 54:3034–3038
    [Google Scholar]
  22. Stafford T.M. 1993 The microbial degradation of chloroalkanes PhD thesis Belfast UK. Belfast: The Queens University;
    [Google Scholar]
  23. Stirling D.J., Dalton H. 1979; The fortuitous oxidation and cometabolism of various carbon compounds by whole-cell suspensions of Methy/ococcus capsulatus (Bath). FEAIS Microbiol Lett 5:315–318
    [Google Scholar]
  24. Stucki G., Galli R., Ebersold H. R., Leisinger T. 1981; Dehalogenation of dichloromethane by cell extracts of Hyphomicrobium DM2. Arch Microbiol 130:366–371
    [Google Scholar]
  25. Vannelli T., Logan M., Arciero D. M., Hooper A. B. 1990; Degradation of halogenated aliphatic compounds by the ammonia-oxidizing bacterium Nitrosomonas europaea. Appl Environ Microbiol 56:1169–1171
    [Google Scholar]
  26. Van den Wijngaard A. J., Van der Kamp K. W. H. J. J., Van der Ploeg J., Pries F., Kazemier B., Janssen D. B. 1992; Degradation of 1,2-dichloroethane by Ancylobacter aquaticus and other facultative methylotrophs. Appl Environ Microbiol 58:976–983
    [Google Scholar]
  27. Vogel T.M., McCarty P. L. 1985; Biotransformation of tetra- chloroethylene to trichloroethylene, dichloroethylene, vinyl chloride and carbon dioxide under methanogenic conditions. Appl Environ Microbiol 49:1080–1083
    [Google Scholar]
  28. Yokota T., Omori T., Kodama T. 1987; Purification and properties of haloalkane dehalogenase from Corjnebacterium sp. strain ml 5-3. J Bacterial 169:4049–4054
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-140-6-1433
Loading
/content/journal/micro/10.1099/00221287-140-6-1433
Loading

Data & Media loading...

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error