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The biodegradation of piperazine and structurally-related linear and cyclic amines

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Abstract

The biodegradability of a range of linear and cyclic amines was assessed. All proved to be biodegradable but there were interesting differences in their susceptibility. The least degradable was piperazine although piperazine-degrading microorganisms were of widespread occurrence in samples of water and activated sludge and, to a lesser extent, soils. Piperazine degraders are only present in very small numbers — on averageca. 0.8/ml of river water. Of six isolates capable of using piperazine as a sole source of carbon, nitrogen and energy in pure culture five were identified asMycobacterium spp. and one asArthrobacter sp., all strains were capable only of slow growth (mean generation time ofca. 30 to 40 hours) on this substrate. Piperidine, pyrrolidine, ethanolamine and diethanolamine were all readily biodegradable. The relationship between structure and degradability of amines is discussed as are the possible reasons for the relative recalcitrance of piperazine.

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References

  • Agarwal M, Roy U & Shukla OP (1988) Piperidine catabolism and Dopa decarboxylase synthesis in aPseudomonas. Biol. Mem. 14: 187–198

    Google Scholar 

  • Anon (1983) Final report on the safety assessment of triethanolamine, diethanolamine and monoethanolamine. J. Am. Coll. Toxicol. 2: 183–234

    Google Scholar 

  • Bartsch H (1991) N-nitroso compounds and human cancer: where do we stand? In: O'Neill, Chen J & Bartsch H (Eds) Relevance to Human Cancer of N-nitroso Compounds, Tobacco Smoke and Mycotoxins. (pp 1–10) International Agency for Research on Cancer, Lyon

    Google Scholar 

  • Brown VR (1988) The microbiology of an activated sludge plant involved in the treatment of xenobiotic compounds. Ph.D. Thesis, University of Leeds, U.K.

    Google Scholar 

  • Brown VR & Knapp JS (1990) The effect of withdrawal of morpholine from the influent and its reinstatement on the performance and microbial ecology of a model activated sludge plant treating a morpholine-containing influent. J. Appl. Bact. 69: 43–53

    Google Scholar 

  • Calmels S, Ohshima H, Vincent P, Gounot A-M & Bartsch H (1985) Screening of microorganisms for nitrosation catalysis at pH 7 and kinetic studies on nitrosamine formation byE. coli strains. Carcinogenesis 6: 911–915

    Google Scholar 

  • Cech JS, Hartman P, Slosarek M & Chudoba J (1988) Isolation and identification of a morpholine-degrading bacterium. Appl. Environ. Microbiol. 54: 619–621

    Google Scholar 

  • Cripps RE & Noble AS (1973) The metabolism of nitrilotriacetate by a pseudomonad. Biochem. J. 136: 1059–1068

    Google Scholar 

  • Dmitrenko GN, Udod VM & Gvozdyak PI (1985) Destruction of morpholine by fixed bacteria. Khim. Teknol. Vody 7: 97–99

    Google Scholar 

  • Dmitrenko GN, Gvozdyak PI & Udod VM (1987) Selection of destructor microorganisms for heterocyclic xenobiotics. Khim. Teknol. Vody 9: 77–81

    Google Scholar 

  • Dmitrenko GN & Gvozdyak PI (1988) Destruction of morpholine by mycobacteria. In: Proceedings of Conference on Microbiological Methods for Protecting the Environment. Centre for Biological Research, Puschino, USSR

    Google Scholar 

  • Dubin DT (1960) The assay and characterization of amines by means of 2,4-dinitrofluorobenzene. J. Biol. Chem. 235: 783–786

    Google Scholar 

  • Edens MR & Lochary JF (1992) Alkanolamines. In: Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 2. 4th edn. (pp 1–26) Wiley Interscience, New York

    Google Scholar 

  • Fattakhova AN, Ofitserov EN & Garusov AV (1991) Cytochrome P-450-dependent catabolism of triethanolamine inRhodotorula mucilaginosa. Biodegradation 2: 107–113

    Google Scholar 

  • Fushiwaki Y & Urano K (1988) Biodegradation test of herbicide in water and sediment using the modified riverwater die-away method. Water Res. 22: 1137–1141

    Google Scholar 

  • Gannon JE, Adams MC & Bennett EO (1978) Microbial degradation of diethanolamine and related compounds. Microbios 23: 7–18

    Google Scholar 

  • Gupta RC, Kaul SM & Shukla OP (1975) Pyrrolidine metabolism and its regulation inArthrobacter sp. Indian J. Biochem. and Biophys. 12: 263–268

    Google Scholar 

  • Jakoby WB & Fredericks J (1959) Pyrrolidine and putrescine metabolism: γ-aminobutyraldehyde dehydrogenase. J. Biol. Chem. 234: 2145–2150

    Google Scholar 

  • Jones A & Turner JM (1973) Microbial metabolism of amino alcohols: 1-aminopropan-2-ol and ethanolamine metabolism via propionaldehyde and acetaldehyde in a species ofPseudomonas. Biochem. J. 134: 167–182

    Google Scholar 

  • Jones A, Faulkener A & Turner JM (1973) Microbial metabolism of amino alcohols: metabolism of ethanolamine and 1-aminopropan-2-ol in a species ofErwinia and the roles of amino alcohol kinase and amino alcohol O-phosphate phospholyase in aldehyde formation. Biochem. J. 134: 959–968

    Google Scholar 

  • Knapp JS & Brown VR (1988) Morpholine biodegradation. Int. Biodeter. 24: 299–306

    Google Scholar 

  • Knapp JS & Whytell A (1990) The biodegradation of morpholine in river water and activated sludge. Environ. Pollut. 68: 67–79

    Google Scholar 

  • Knapp JS, Callely AG & Mainprize JH (1982) The microbial degradation of morpholine. J. Appl. Bact. 52: 5–13

    Google Scholar 

  • Kornberg HL (1966) Anaplerotic sequences and their role in metabolism. Essays in Biochem. 2: 1–31

    Google Scholar 

  • Large PJ (1971) The oxidative cleavage of alkyl-nitrogen bonds in microorganisms. Xenobiotica 1: 457–467

    Google Scholar 

  • McKenzie P & Hughes DE (1976) Microbial degradation of oil and petrochemicals in the sea. In: Skinner FA & Carr JG (Eds) Microbiology of Agriculture, Fisheries and Food. Soc. Appl. Bact. Symp. 4 (pp 91–108) Academic Press, London

    Google Scholar 

  • Mirvish SS (1975) Formation of N-nitroso compounds: Chemistry, kinetics, and in vivo occurrence. Toxicol. and Appl. Pharmacol. 31: 325–351

    Google Scholar 

  • Mjos K (1978) Cyclic amines. In: Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 2. 3rd edn. (pp 295–308) Wiley Interscience, New York

    Google Scholar 

  • National Research Council (1981) Selected aliphatic amines and related compounds: an assessment of the biological and environmental effects. National Academy Press, Washington, D.C.

    Google Scholar 

  • Pitter P & Chudoba J (1990) Biodegradability of organic substances in the aquatic environment. CRC Press, Boca Raton

    Google Scholar 

  • Roof DM & Roth JR (1988) Ethanolamine utilization inSalmonella typhimurium. J. Bacteriol. 170: 3855–3863

    Google Scholar 

  • Rothkopf & Bartha (1984) Structure-biodegradability correlations among xenobiotic industrial amines. JAOCS 61: 977–980

    Google Scholar 

  • Scarlett FA & Turner JM (1976) Microbial metabolism of amino alcohols. Ethanolamine catabolism mediated by co-enzyme B12-dependent ethanolamine ammonia lyase inEscherichia coli andKlebsiella aerogenes. J. Gen. Microbiol. 95: 173–176

    Google Scholar 

  • Stevens & Skov (1965) A rapid spectrophotometric method for determining parts per million of morpholine in boiler water. Analyst 90: 182–183

    Google Scholar 

  • Swain A, Waterhouse KV, Venables WA, Callely AG & Lowe SE (1991) Biochemical studies of morpholine catabolism by an environmental mycobacterium. Appl. Microbiol. Biotechnol. 35: 110–114

    Google Scholar 

  • Tiedje JM, Mason BB, Warren CB & Malec EJ (1973) Metabolism of nitrilotriacetate by cells ofPseudomonas species. Appl. Microbiol. 25: 811–818

    Google Scholar 

  • Turcotte MG & Johnson TA (1992) Amines (lower aliphatic). In: Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 2. 4th edn. (pp 369–386) Wiley Interscience, New York

    Google Scholar 

  • Williams GR & Callely AG (1982) The biodegradation of diethanolamine and triethanolamine by a yellow Gram-negative rod. J. Gen. Microbiol. 128: 1203–1209

    Google Scholar 

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Emtiazi, G., Knapp, J.S. The biodegradation of piperazine and structurally-related linear and cyclic amines. Biodegradation 5, 83–92 (1994). https://doi.org/10.1007/BF00700633

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