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Metabolite detection in Rhodococcus benzothiophene desulfurization using reversed-phase solid-phase extraction and a derivatization technique

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Abstract

Hydrophilic benzo[b]thiophene metabolites produced by Rhodococcus sp. strain T09 were isolated by a solid-phase extraction and a derivatization method, which prevented the dehydration that often occurs during liquid-liquid extraction (LLE), and were identified by GC with atomic emission detection and GC-MS. As a result, cis- or trans-2-(2′-hydroxyphenyl) ethen-1-ol, previously reported as the tautomer 2-(2′-hydroxyphenyl) ethan-1-al, and 2-(2′-hydroxyphenyl) ethen-1-sulfenic acid and its isomer, 1-(1′-hydroxyethenyl) benzene-2-sulfenic acid, were identified. Benzothiophene desulfurization in culture broth at neutral pH by the strain T09 was modified as a branched metabolism from benzothiophene S-oxide based on the above compounds.

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References

  • Gilbert SC, Morton J, Buchanan JS, Oldfield C, McRobert A (1998) Isolation of a unique benzothiophene-desulfurizing bacterium, Gordona sp. strain 213E (NCIMB40816), and characterization of the desulphurization pathway. Microbiology 144: 2545–2553.

    Google Scholar 

  • Hashimoto N, Aoyama T, Shioiri T (1981) New methods and reagents in organic synthesis. 14. A simple efficient preparation of methyl esters with trimethylsilyldiazomethane (TMSCHN2) and its application to gas chromatographic analysis of fatty acids. Chem. Pharm. Bull. 29: 1475–1478.

    Google Scholar 

  • Izumi Y, Ohshiro T, Ogino H, Hine Y, Shimao M (1994) Selective desulfurization of dibenzothiophene by Rhodococcus erythropolis D-1. Appl. Environ. Microbiol. 60: 223–226.

    Google Scholar 

  • Konishi J, Onaka T, Ishii Y, Suzuki M (2000) Demonstration of the carbon-sulfur bond targeted desulfurization of benzothiophene by thermophilic Paenibacillus sp. strain A11-2 capable of desulfurizing dibenzothiophene. FEMS Microbiol. Lett. 187: 151–154.

    Google Scholar 

  • Matsui T, Hirasawa K, Koizumi K-I, Maruhashi K, Kurane R (2001) Dibenzothiophene desulfurizing genes copy number optimization to increase the desulfurization activity of recombinant Rhodococcus sp. Biotechnol. Lett. 23: 1715–1718.

    Google Scholar 

  • Matsui T, Onaka T, Maruhashi K, Kurane R (2001) Benzo[b]thiophene desulfurization by Gordonia rubropertinctus strain T08. Appl. Microbiol. Biotechnol. 57: 212–215.

    Google Scholar 

  • Matsui T, Onaka T, Tanaka Y, Tezuka T, Suzuki M, Kurane R (2000) Alkylated benzothiophene desulfurization by Rhodococcus sp. strain T09. Biosci. Biotechnol. Biochem. 64: 596–599.

    Google Scholar 

  • Monticello DJ (1998) Riding the fossil fuel biodesulfurization wave.ChemTech 28: 38–45.

    Google Scholar 

  • Onaka T, Okumura K, Suzuki M (1997) Analysis of biodesulfurization products using solid-phase extraction. J. Chromatogr. Sci. 35: 417–422.

    Google Scholar 

  • Tanaka T, Onaka T, Matsui T, Maruhashi K, Kurane R (2001) Desulfurization of benzothiophene by the gram-negative bacterium, Sinorhizobium sp. KT55. Curr. Microbiol. 43: 187–191.

    Google Scholar 

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Onaka, T., Matsui, T. & Maruhashi, K. Metabolite detection in Rhodococcus benzothiophene desulfurization using reversed-phase solid-phase extraction and a derivatization technique. Biotechnology Letters 24, 1961–1966 (2002). https://doi.org/10.1023/A:1021154528924

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  • DOI: https://doi.org/10.1023/A:1021154528924

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