Isolation of a unique benzothiophene-desulphurizing bacterium, Gordona sp. strain 213E (NCIMB 40816), and characterization of the desulphurization pathway Free

Abstract

sp. strain 213E (NCIMB 40816) grew in pure culture in a mineral salts medium containing fructose as a source of carbon and energy, and benzothiophene (BTH) as the sole source of sulphur. During growth a phenolic compound accumulated, as indicated by the production of a blue colour on addition of Gibb's reagent. Therefore this pathway is analogous to the dibenzothiophene (DBT) desulphurization pathway of sp. strain IGTS8, in which 2-hydroxybiphenyl accumulates during growth with DBT as the sole sulphur source. Ethyl acetate extraction of the culture medium yielded the metabolites benzothiophene -oxide (BTHO), benzothiophene -dioxide (BTHO), benzo[c][1,2]oxathiin 6-oxide (BcOTO), 2-(2'-hydroxyphenyl)ethan 1-al (HPEal) and benzofuran (BFU). The deduced pathway for BTH desulphurization is BTH ? BTHO ? BTHO ? HPESi ? HPEal. HPESi is (Z)-2-(2'-hydroxyphenyl)ethen 1-sulphinate, the stable aqueous-solution form of BcOTO. It was concluded that HPEal was the Gibb's-reagent-reactive phenolic compound which accumulated in the culture medium of strain 213E during growth, and that the presence of BFU was due to partial condensation of HPEal during the ethyl acetate extraction procedure. sp. strain 213E was unable to grow in a mineral salts medium containing fructose as a source of carbon and energy and DBT as the sole sulphur source. BTH-desulphurization-active cells (grown using BTH as sole sulphur source) were unable to desulphurize DBT. Likewise sp. strain IGTS8 was unable to grow using BTH as the sole sulphur source, and DBT-desulphurization-active cells of strain IGTS8 (grown using DBT as sole sulphur source) were unable to desulphurize BTH. This absence of cross-reactivity is discussed in terms of fundamental differences in the chemistry of the DBT- and BTH-desulphurization reactions.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-144-9-2545
1998-09-01
2024-03-29
Loading full text...

Full text loading...

/deliver/fulltext/micro/144/9/mic-144-9-2545.html?itemId=/content/journal/micro/10.1099/00221287-144-9-2545&mimeType=html&fmt=ahah

References

  1. Asturias J.A., Eltis L.D., Prucha M., Timmis K.M. 1994; Analysis of three 2,3-dihydroxybiphenyl 1,2-dioxygenases found in Rhodococcus globerulus P6.. Biol Chem 269:7807–7815
    [Google Scholar]
  2. Beil S., Kehrli H., James P., Staudenmann W., Cook A.M., Leisinger T., Kertesz M.A. 1995; Purification and charac-terisation of the arylsulfatase synthesised by Pseudomonas aeruginosa PAO during growth in sulfate-free medium and cloning of the arylsulfatase gene (atsA).. Eur J Biochem 229:385–394
    [Google Scholar]
  3. Bowie J.H., Williams D.H., Lawesson S.-O., Madsen J.ø., Nolde C., Schroll G. 1966; Studies in mass spectrometry. XV. Mass spectra of sulphoxides and sulphones. The formation of C-C and C-O bonds upon electron impact.. Tetrahedron 22:3515–3525
    [Google Scholar]
  4. Chiang Y., Kresge A.J., Walsh P.A., Yin Y. 1989; Phenyl- acetaldehyde and its cis- and trans-enols and enolate ions. Determination of the cis: trans ratio under equilibrium and kinetic control.. J Chem Soc Chem Commun869–871
    [Google Scholar]
  5. Constanti M., Girlat J., Bordons A. 1996; Degradation and desulfurization of dibenzothiophene sulfone and other sulfur compounds by Agrobacterium MC501 and a mixed culture.. Enzyme Microb Technol 19:214–219
    [Google Scholar]
  6. Denis-Larose C., Labbe D., Nergeron H., Jones A.M., Greer C.W., Al-Hawari J., Grossman M.J., Sankey B.M., Lau P.C.K. 1997; Conservation of plasmid-encoded dibenzothiophene desulphurisation genes in several rhodococci.. Appl Environ Microbiol 63:2915–2919
    [Google Scholar]
  7. Denome S.A., Olson E.S., Young K.D. 1993; Identification and cloning of genes involved in specific desulphurisation of dibenzothiophene by Rhodococcus sp. strain IGTS8.. Appl Environ Microbiol 59:2837–2843
    [Google Scholar]
  8. Denome S.A., Oldfield C., Nash L.J., Young K. 1994; Characterisation of the desulfurization genes from Rhodococcus sp. strain IGTS8.. J Bacteriol 176:6707–6716
    [Google Scholar]
  9. Fields E.K., Meyerson S. 1966; Pyrolysis and mass spectrum of dibenzothiophene 5,5-dioxide.. J Am Chem Soc 88:2836–2837
    [Google Scholar]
  10. Gray K.A., Pogrebinsky O., Mrashko G.T., Xi L., Monticello D.J., Squires C.H. 1996; Molecular mechanisms of biocatalytic desulphurisation of fossil fuels.. Nat Biotechnol 14:1705–1708
    [Google Scholar]
  11. Hanson G., Kemp D.S. 1981; Convenient routes to 4,4“ functionalised o-terphenyls and 2,2’ functionalised biphenyls.. J Org Chem 46:5441–5443
    [Google Scholar]
  12. Izumi Y., Ohshiro T., Ogino H., Hine Y., Shimao M. 1994; Selective desulfurization of dibenzothiophene by Rhodococcus erythropolis strain D-l.. Appl Environ Microbiol 60:223–226
    [Google Scholar]
  13. Joule J.A., Mills K., Smith G.F. 1995 Heterocyclic Chemistry, 3rd edn. p. 355 London: Chapman &Hall;
    [Google Scholar]
  14. Kayser K.J., Bielaga-Jones B.A., Jackowski K., Odusan O., Kilbane J.J. 1993; Utilization of organosulphur compounds by axenic and mixed cultures of Rbodococcus rbodochrous strain IGTS8.. J Gen Microbiol 139:3123–3129
    [Google Scholar]
  15. Konishi J., Ishii Y., Onaka T., Okumura K., Suzuki M. 1997; Thermophilic carbon-sulphur bond targeted biodesulfurisation.. Appl Environ Microbiol 63:3164–3169
    [Google Scholar]
  16. Kosono S., Maeda M., Fuji F., Arai H., Kudo T. 1997; Three of the seven bphC genes of Rbodococcus erytbropolis TA421, isolated from a termite ecosystem, are located on an indigenous plasmid associated with biphenyl degradation.. Appl Environ Microbiol 63:3283–3285
    [Google Scholar]
  17. Lee M.K., Senius J.D., Grossman M.J. 1995; Sulfur-specific microbial desulfurization of sterically hindered analogs of dibenzothiophene.. Appl Environ Microbiol 61:4362–4366
    [Google Scholar]
  18. Lei B., Tu S.-C. 1996; Gene overexpression, purification and identification of a desulfurization enzyme from Rbodococcus sp. strain IGTS8 as a sulfide/sulfoxide monooxygenase.. J Bacteriol 17:5699–5705
    [Google Scholar]
  19. Li M.Z., Squires C.H., Childs J.D. 1996; Genetic analysis of the dsz promoter and associated regulatory regions of Rbodococcus erytbropolis IGTS8.. J Bacteriol 178:6409–6418
    [Google Scholar]
  20. Masai E., Sugiyama K., Iwashite N., Shimizu S., Hauschild J.E., Hatta T., Kimbara K., Yano K., Fukuda M. 1997; The bphDEF meta-cleavage pathway genes involved in biphenyl/ polychlorinated biphenyl degradation are located on a linear plasmid and separated from the initial bphhCB genes in Rbodococcus sp. strain RHA1.. Gene 187:141–149
    [Google Scholar]
  21. Nekodzuka S., Toshiaki N., Nakajima-Kambe T., Nobura N., Lu J., Nakahara Y. 1997; Specific desulphurisation of dibenzo-thiophene by Mycobacterium strain G3 Biocatalysis Biotransformation . 15:21–27
    [Google Scholar]
  22. Ohshiro T., Hirata T., Izumi Y. 1996a; Desulfurization of dibenzothiophene derivatives by whole cells of Rbodococcus erytbropolis strain H-2.. FEMS Microbiol Lett 142:65–70
    [Google Scholar]
  23. Ohshiro T., Suzuki K., Izumi Y. 1996b; Regulation of dibenzothiophene-degrading activity of Rbodococcus erythro- polis strain D-l.. J Ferment Bioeng 81:121–124
    [Google Scholar]
  24. Oldfield C., Pogrebinsky O., Simmonds J., Olson E, Kulpa C.F. 1997; Elucidation of the metabolic pathway for dibenzo-thiophene desulphurisation by Rbodococcus sp. strain IGTS8 (ATCC 53968).. Microbiology 143:2961–2973
    [Google Scholar]
  25. Olson E.S., Stanley D.C., Gallagher J.R. 1993; Charac-terisation of intermediates in the microbial desulfurization of dibenzothiophene.. Energy & Fuels 7:159–164
    [Google Scholar]
  26. Omori T., Monna L., Saiki Y., Kodama T. 1992; Desulfurization of dibenzothiophene by Corynebacterium sp. strain SY1.. Appl Environ Microbiol 58:911–915
    [Google Scholar]
  27. Omori T., Saiki Y., Kasuga K., Kodama T. 1995; Desulfurization of alkyl and aromatic sulfides and sulfonates by dibenzothiophene desulphurising Rbodococcus sp. strain SY1 Biosci Biotechnol Biochem . 59:1195–1198
    [Google Scholar]
  28. van der Ploeg J.R., Iwanikca-Nowicka R., Kertesz M.A., Leisinger T., Hoyniewicz M.M. 1998; Involvement of CysB and Cbl regulatory proteins in the tauABCD operon and other sulphate starvation inducible genes in Escherichia coli.. J Bacteriol 179:7671–7678
    [Google Scholar]
  29. Purdy R.F., Lepo J.E., Ward B. 1993; Biodesulphurisadon of organic sulphur compounds.. Curr Microbiol 27:219–222
    [Google Scholar]
  30. Rhee S.-K., Chang J.H., Chang Y.K., Chang H.O. 1998; Desulfurization of dibenzothiophene and diesel oils by a newly isolated Gordona strain, CYKS1.. Appl Environ Microbiol 64:2327–2331
    [Google Scholar]
  31. Wang P., Krawiec S. 1996; Kinetic analyses of desulfurization of dibenzothiophene by Rbodococcus erytbropolis in batch and fed-batch cultures Appl Environ Microbiol . 62:3066–3068
    [Google Scholar]
  32. Wang P., Humphrey A.E., Krawiec S. 1996; Kinetic analyses of desulfurization of dibenzothiophene by Rbodococcus erytbropolis in continuous cultures.. Appl Environ Microbiol 62:3066–3068
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-144-9-2545
Loading
/content/journal/micro/10.1099/00221287-144-9-2545
Loading

Data & Media loading...

Most cited Most Cited RSS feed