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Degradation pathways of cyclic alkanes in Rhodococcus sp. NDKK48

  • Applied Microbial and Cell Physiology
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Abstract

The degradation pathways for cyclic alkanes (c-alkanes) in Rhodococcus sp. NDKK48 were investigated. Strain NDKK48 used dodecylcyclohexane as a sole carbon and energy source, and five metabolites in the dodecylcyclohexane degradation pathway were detected by gas-chromatography/mass spectra. The metabolites were identified as cyclohexanecarboxylic acid, cyclohexylacetic acid, 1-cyclohexene-1-acetic acid, 4-dodecylcyclohexanol, and 4-dodecylcyclohexanone. The strain degrades dodecylcyclohexane via a ring oxidation pathway and an alkyl side chain oxidation pathway. Cyclohexanecarboxylic acid was further oxidized to muconic acid via 1-cyclohexene-1-carboxylic acid and benzoic acid, and the muconic acid was finally used by strain NDKK48 for growth. Methylcyclohexane and cyclohexane were co-oxidized with hexadecane by strain NDKK48. Methylcyclohexane was degraded via a ring oxidation pathway, and the degradation pathway contained part of the Baeyer-Villiger oxidation for ring cleavage. Cyclohexane was also degraded by the same pathway as methylcyclohexane. Thus, strain NDKK48 has two pathways for the complete degradation of c-alkanes.

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References

  • Abbott BJ, Gledhill WE (1971) Extracellular accumulation of metabolic products by hydrocarbon-degrading microorganisms. Adv Appl Microbiol 14:249–388

    CAS  PubMed  Google Scholar 

  • Beam HW, Perry JJ (1974) Microbial degradation and assimilation of n-alkyl-substituted cycloparaffins. J Bacteriol 118:394–399

    CAS  PubMed  Google Scholar 

  • Blakley ER (1978) The microbial degradation of cyclohexanecarboxylic acid by a β-oxidation pathway with simultaneous induction to the utilization of benzoate. Can J Microbiol 24:847–855

    CAS  PubMed  Google Scholar 

  • Blakley ER, Papish B (1982) The metabolism of cyclohexanecarboxylic acid and 3-cyclohexenecarboxylic acid by Pseudomonas putida. Can J Microbiol 28:1324–1329

    CAS  PubMed  Google Scholar 

  • Butler CS, Mason JR (1997) Structure-function analysis of the bacterial aromatic ring-hydroxylating dioxygenases. Adv Microb Physiol 38:47–84

    CAS  PubMed  Google Scholar 

  • Clarke PH (1984) The evolution of degradative pathways. In: Gibson DT (ed) Microbial degradation of organic compounds. Dekker, New York, pp 11–27

  • Doboghue NA, Norris D, Trudgill PW (1976) The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB9871. Eur J Biochem 63:175–192

    CAS  PubMed  Google Scholar 

  • Dong JZ, Vorkink WP, Lee ML (1993) Origin of long-chain alkylcyclohexanes and alkylbenzenes in a coal-bed wax. Geochim Cosmochim Acta 57:837–849

    Article  CAS  Google Scholar 

  • Donoghue NA, Trudgill PW (1975) The metabolism of cyclohexanol by Acinetobacter NCIB 9871. Eur J Biochem 60:1–7

    CAS  PubMed  Google Scholar 

  • Dutta TK, Harayama S (2001) Biodegradation of n-alkylcycloalkanes and n-alkylbenzenes via new pathways in Alcanivorax sp. strain MBIC4326. Appl Environ Microbiol 67:1970–1974

    Article  CAS  PubMed  Google Scholar 

  • Elshahed MS, Bhupathiraju VK, Wofford NQ, Nanny MA, McInerney MJ (2001) Metabolism of benzoate, cyclohex-1-ene carboxylate, and cyclohexane carboxylate by Syntrophus aciditrophicus strain SB in syntrophic association with H2-using microorganisms. Appl Environ Microbiol 67:1728–1738

    Google Scholar 

  • Fowler MG, Abolins P, Douglas AG (1986) Monocyclic alkanes in Ordovician organic matter. Org Geochem 10:815–823

    CAS  Google Scholar 

  • Griffin M, Trudgill PW (1976) Purification and properties of cyclopentanone oxygenase of Pseudomonas NCIB9872. Eur J Biochem 63:199–209

    CAS  PubMed  Google Scholar 

  • Hasegawa Y, Nakai Y, Tokuyama T, Iwaki H (2000) Purification and characterization of cyclohexanone 1,2-monooxygenase from Exophiala jeanselmei strain KUIN-6N. Biosci Biotechnol Biochem 64:2696–2698

    CAS  PubMed  Google Scholar 

  • Kaneda T, Obata H, Tokumoto M (1993) Aromatization of 4-oxocyclohexanecarboxylic acid to 4-hydroxybenzoic acid by two distinctive desaturases from Corynebacterium cyclohexanicum—properties of two desaturases. Eur J Biochem 218:997–1003

    CAS  PubMed  Google Scholar 

  • Kissin YV (1990) Catagenesis of light cycloalkanes in petroleum. Org Geochem 15:575–594

    Article  CAS  Google Scholar 

  • Ko SH, Lebeault JM (1999) Effect of a mixed culture on co-oxidation during the degradation of saturated hydrocarbon mixture. J Appl Microbiol 87:72–79

    Article  CAS  PubMed  Google Scholar 

  • Koma D, Sakashita Y, Kubota K, Fujii Y, Hasumi F, Chung SY, Kubo M (2003a) Degradation of car engine base oil by Rhodococcus sp. NDKK48 and Gordonia sp. NDKY76A. Biosci Biochem Bioeng 67:1590–1593

    Article  CAS  Google Scholar 

  • Koma D, Hasumi F, Chung SY, Kubo M (2003b) Biodegradation of n-alkylcyclohexanes by co-oxidation via multiple pathways in Acinetobacter sp. ODDK71. J Biosci Bioeng 95:641–644

    CAS  Google Scholar 

  • Komukai-Nakamura S, Sugiura K, Yamauchi-Inomata Y, Toki H, Venkateswaran K, Yamamoto S, Tanaka H, Harayama S (1996) Construction of bacterial consortia that degrade Arabian light crude oil. J Ferment Bioeng 82:570–574

    Article  CAS  Google Scholar 

  • Kostichka K, Thomas SM, Gibson KJ, Nagarajan V, Cheng Q (2001) Cloning and characterization of a gene cluster for cyclododecanone oxidation in Rhodococcus ruber SC1. J Bacteriol 183:6478–6486

    CAS  PubMed  Google Scholar 

  • Lal B, Khanna S (1996) Degradation of crude oil by Acinetobacter calcoaceticus and Alcaligenes odorans. J Appl Bacteriol 81:355–362

    CAS  PubMed  Google Scholar 

  • Ougham HJ, Trudgill PW (1982) Metabolism of cyclohexaneacetic acid and cyclohexanebutyric acid by Arthrobacter sp. strain CA1. J Bacteriol 150:1172–1182

    CAS  PubMed  Google Scholar 

  • Perry JJ (1984) Microbial metabolism of cyclic alkanes. In: Atlas RM (ed) Petroleum microbiology. Macmillan, New York, pp 61–98

  • Rehm H, Reiff I (1981) Mechanism and occurrence of microbial oxidation of long chain alkanes. Adv Biochem Eng 19:175–215

    CAS  Google Scholar 

  • Schumacher JD, Fakoussa RM (1999) Degradation of alicyclic molecules by Rhodococcus ruber CD4. Appl Microbiol Biotechnol 52:85–90

    Article  CAS  PubMed  Google Scholar 

  • Stirling LA, Watkinson RJ (1977) Microbial metabolism of alicyclic hydrocarbons: isolation and properties of a cyclohexane-degrading bacterium. J Gen Microbiol 99:119–125

    CAS  Google Scholar 

  • Swannell RPJ, Lee K, McDonagh M (1996) Field evaluations of marine oil spill bioremediation. Microbiol Rev 60:342–365

    CAS  PubMed  Google Scholar 

  • Trower MK, Buckland RM, Griffin M (1989) Characterization of an FMN-containing cyclohexanone monooxygenase from a cyclohexane-grown Xanthobacter sp. Eur J Biochem 181:191–206

    Google Scholar 

  • Williams JA, Dolcater DL, Torkelson BE, Winters JC (1988) Anomalous concentrations of specific alkylaromatics and alkylcycloparaffin components in West Texas and Michigan crude oils. Org Geochem 13:47–59

    Article  CAS  Google Scholar 

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Koma, D., Sakashita, Y., Kubota, K. et al. Degradation pathways of cyclic alkanes in Rhodococcus sp. NDKK48. Appl Microbiol Biotechnol 66, 92–99 (2004). https://doi.org/10.1007/s00253-004-1623-5

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  • DOI: https://doi.org/10.1007/s00253-004-1623-5

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