Transformation and biodegradation of 1,2,3-trichloropropane (TCP)

Environmental Science and Pollution Research

Volumn 19, Issue 8, 2012, Pages 3067-3078

  Samin, Ghufrana ^a   Janssen, Dick B ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

1,2,3 Trichloropropane; Biodegradation; Bioremediation; Chlorinated hydrocarbons; Dehalogenase

Indexed keywords

1,2,3 TRICHLOROPROPANE; 1,2,3-TRICHLOROPROPANE; CARCINOGEN; DRUG DERIVATIVE; PROPANE; ZINC;

BIODEGRADATION; BIOREMEDIATION; CARCINOGEN; CHLORINATED HYDROCARBON; CLEANUP; DECHLORINATION; ENZYME ACTIVITY; GROUNDWATER POLLUTION; HAZARDOUS WASTE; INDUSTRIAL WASTE; MINERALIZATION; OXIC CONDITIONS; TOXICITY; TRANSFORMATION; XENOBIOTICS;

ANIMAL; ARTICLE; BACTERIUM; BIOREMEDIATION; CHEMISTRY; GENETICS; HUMAN; METABOLIC ENGINEERING; METABOLISM; METHODOLOGY; PROTEIN ENGINEERING; WATER POLLUTANT;

ANIMALS; BACTERIA; BIODEGRADATION, ENVIRONMENTAL; CARCINOGENS; HUMANS; METABOLIC ENGINEERING; PROPANE; PROTEIN ENGINEERING; WATER POLLUTANTS; ZINC;

EID: 84865540137     PISSN: 09441344     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11356-012-0859-3     Document Type: Article

References (78)

1. ATSDR (1992) Toxicological profile for 1, 2, 3-trichloropropane. http://www. atsdr. cdc. gov/toxprofiles/tp57. pdf. Accessed December 23, 2011.
2. ATSDR (2011) Addendum to the toxicological profile for 1, 2, 3-trichloropropane. http://www. atsdr. cdc. gov/toxprofiles/123-Trichloropropane_addendum. pdf. Accessed December 23, 2011.
3. Bosma T, Janssen DB (1998) Conversion of chlorinated propanes by Methylosinus trichosporium OB3b expressing soluble methane monooxygenase. Appl Microbiol Biotechnol 50: 105-112.
4. Bosma T, Kruizinga E, de Bruin EJ, Poelarends GJ, Janssen DB (1999) Utilization of trihalogenated propanes by Agrobacterium radiobacter AD1 through heterologous expression of the haloalkane dehalogenase from Rhodococcus sp strain m15-3. Appl Environ Microbiol 65: 4575-4581.
5. Bosma T, Damborsky J, Stucki G, Janssen DB (2002) Biodegradation of 1, 2, 3-trichloropropane through directed evolution and heterologous expression of a haloalkane dehalogenase gene. Appl Environ Microbiol 68: 3582-3587.
6. California Environmental Protection Agency (2009) Public health goal for 1, 2, 3-trichloropropane in drinking water. http://www. oehha. ca. gov/water/phg/pdf/082009TCP_phg. pdf. Accessed December 24, 2011.
7. CH2M Hill (2005) Interim guidance for investigating potential 1, 2, 3-trichloropropane sources in San Gabriel valley area 3. EPA contr no 68-W-98-225.
8. de Lorenzo V (2009) Recombinant bacteria for environmental release: what went wrong and what we have learnt from it. Clin Microbiol Infect 15: 63-65.
9. de Lorenzo V, Timmis KN (1994) Analysis and construction of stable phenotypes in Gram-negative bacteria with Tn5-derived and Tn10-derived minitransposons. Methods Enzymol 235: 386-405.
10. de Wildeman S, Diekert G, van Langenhove H, Verstraete W (2003) Stereoselective microbial dehalorespiration with vicinal dichlorinated alkanes. Appl Environ Microbiol 69: 5643-5647.
11. Dolfing J, Janssen DB (1994) Estimates of Gibbs free energies of formation of chlorinated aliphatic compounds. Biodegradation 5: 21-28.
12. Dombeck G, Brog C (2005) Multi-contaminant treatment for 1, 2, 3-trichloropropane destruction using the HiPOx reactor. Proceedings of NGWA conference on MTBE and perchlorate. In: Proceedings of the Sixth International Conference on Remediation of Chlorinated and Recalcitrant Compounds, May 2008, Monterey, CA.
13. ECHA (2012a): European Chemicals Agency. SHVC Support Document. http://echa. europa. eu/documents/10162/17230/supdoc_trichloropropane_20110520_en. pdf. Accessed February 22, 2012.
14. ECHA (2012b): European Chemicals Agency. Registered Substances Database. http://echa. europa. eu/web/guest/information-on-chemicals/registered-substances. Accessed February 22, 2012.
15. Effendi AJ, Greenaway SD, Dancer BN (2000) Isolation and characterization of 2, 3-dichloro-1-propanol-degrading Rhizobia. Appl Environ Microbiol 66: 2882-2887.
16. Ewell WS, Gorsuch JW, Kringle RO, Robillard KA, Spiegel RC (1986) Simultaneous evaluation of the acute effects of chemicals on seven aquatic species. Environ Toxicol Chem 5: 831-840.
17. FFRRO. Emerging Contaminant -1, 2, 3-Trichloropropane (TCP). Fact Sheet. http://www. epa. gov/fedfac/documents/emerging_contaminant_tcp. pdf. Accessed December 23, 2011.
18. Gray KA, Richardson TH, Kertz K, Short JM, Bartnek F, Knowles R, Kan L, Swanson PE, Robertson DE (2001) Rapid evolution of reversible denaturation and elevated melting temperature in a microbial haloalkane dehalogenase. Adv Synth Catal 343: 607-617.
19. Hanson RS, Tsien HC, Tsuji K, Brusseau GA, Wackett LP (1990) Biodegradation of low-molecular-weight halogenated hydrocarbons by methanotrophic bacteria. FEMS Microbiol Rev 7: 273-278.
20. Hauck R, Hegemann W (2000) Anaerobic degradation of 1, 2-dichloropropane in batch and continuous culture. Water Sci Technol 41: 7-13.
21. Higgins TP, Hope SJ, Effendi AJ, Dawson S, Dancer BN (2005) Biochemical and molecular characterization of the 2, 3-dichloro-1-propanol dehalogenase and stereospecific haloalkanoic dehalogenases from a versatile Agrobacterium sp. Biodegradation 16: 485-492.
22. HSDB (2000) Hazardous Substances Data Bank. http://toxnet. nlm. nih. gov/cgi-bin/sis/htmlgen?HSBD. Accessed December 22, 2011.
23. Irwin RD, Haseman JK, Eustis SL (1995) 1, 2, 3-Trichloropropane: a multisite carcinogen in rats and mice. Fundam Appl Toxicol 25: 241-252.
24. Janssen DB (2004) Evolving haloalkane dehalogenases. Curr Opin Chem Biol 8: 150-159.
25. Janssen DB, Dinkla IJT, Poelarends GJ, Terpstra P (2005) Bacterial degradation of xenobiotic compounds: evolution and distribution of novel enzyme activities. Environ Microbiol 7: 1868-1882.
26. Khan E, Wirojanagud W, Sermsai N (2009) Effects of iron type in Fenton reaction on mineralization and biodegradability enhancement of hazardous organic compounds. J Hazard Mater 161: 1024-1034.
27. Klausen J, Vikesland PJ, Kohn T, Burris DR, Ball WP, Roberts AL (2003) Longevity of granular iron in groundwater treatment processes: solution composition effects on reduction of organohalides and nitroaromatic compounds. Environ Sci Technol 37: 1208-1218.
28. Koudelakova T, Chovancova E, Brezovsky J, Monincova M, Fortova A, Jarkovsky J, Damborsky J (2011) Substrate specificity of haloalkane dehalogenases. Biochem J 435: 345-354.
29. Krooshof GH, Ridder IS, Tepper AWJW, Vos GJ, Rozeboom HJ, Kalk HK, Dijkstra BW, Janssen DB (1998) Kinetic analysis and X-ray structure of haloalkane dehalogenase with a modified halide-binding site. Biochemistry 37: 15013-15023.
30. Kulakova AN, Larkin MJ, Kulakov LA (1997) The plasmid-located haloalkane dehalogenase gene from Rhodococcus rhodochrous NCIMB 13064. Microbiol 143: 109-115.
31. Kurata A, Kurihara T, Kamachi H, Esaki N (2005) 2-Haloacrylate reductase, a novel enzyme of the medium chain dehydrogenase/reductase superfamily that catalyzes the reduction of a carbon-carbon double bond of unsaturated organohalogen compounds. J Biol Chem 280: 20286-20291.
32. La DK, Lilly PD, Anderegg RJ, Swenberg JA (1995) DNA adduct formation in B6C3F1 mice and Fischer-344 rats exposed to 1, 2, 3-trichloropropane. Carcinogenesis 16: 1419-1424.
33. Lagas P, Verdam B, Loch JPG (1989) Threat to groundwater quality by pesticides in the Netherlands. In: Groundwater management: Quantity and quality (Proceedings of the Benidorm Symposium, October 1989). IAHS Publication No. 188: 171-180.
34. Leahy J, Tracy K, Eley M (2003) Degradation of volatile hydrocarbons from steam-classified solid waste by a mixture of aromatic hydrocarbon-degrading bacteria. Biotechnol Lett 25: 479-483.
35. Liska I, Barceló D, Grasserbauer M (1996) Strategy for the screening of organic pollutants in a river basin-an overview of the Nitra river monitoring programme. Trends Anal Chem 15: 326-334.
36. Löffler FE, Champine JE, Ritalahti KM, Sprague SJ, Tiedje JM (1997) Complete reductive dechlorination of 1, 2-dichloropropane by anaerobic bacteria. Appl Environ Microbiol 63: 2870-2875.
37. Long JL, Stensel HD, Ferguson JF, Strand SE, Ongerth JE (1993) Anaerobic and aerobic treatment of chlorinated aliphatic compounds. J Environ Eng 119: 300-320.
38. Mahmood N, Overstreet D, Burka LT (1991) Comparative disposition and metabolism of 1, 2, 3-trichloropropane in rats and mice. Drug Metab Disposition 19: 411-418.
39. Miermans CJH, van der Velde LE, Frintrop PCM (2000) Analysis of volatile organic compounds, using the purge and trap injector coupled to a gas chromatograph/ion-trap mass spectrometer: Review of the results in Dutch surface water of the Rhine, Meuse, Northern Delta Area and Westerscheldt, over the period 1992-1997. Chemosphere 40: 39-48.
40. Moe WM, Yan J, Nobre MF, da Costa MS, Rainey FA (2009) Dehalogenimonas lykanthroporepellens gen. nov., sp. nov., a reductive dehalogenating bacterium isolated from chlorinated solvent contaminated groundwater. Int J Syst Evol Microbiol 59: 2692-2697.
41. Monincová M, Prokop Z, Vévodová J, Nagata Y, Damborsky J (2007) Weak activity of haloalkane dehalogenase LinB with 1, 2, 3-trichloropropane revealed by X-ray crystallography and microcalorimetry. Appl Environ Microbiol 73: 2005-2008.
42. Mowafy AM, Kurihara T, Kurata A, Uemura T, Esaki N (2010) 2-Haloacrylate hydratase, a new class of flavoenzyme that catalyzes the addition of water to the substrate for dehalogenation. Appl Environ Microbiol 76: 6032-6037.
43. National Toxicology Program (1993) NTP Toxicology and carcinogenesis of 1, 2, 3-trichloropropane (CAS No 96-18-4) in F344/N rats and B6C3F1 mice (Gavage studies). Natl Toxicol Program Tech Rep Ser 384: 1-348.
44. National Toxicology Program (2005) NTP carcinogenesis studies of 2, 2-bis(bromomethyl)-1, 3-propanediol, nitromethane, and 1, 2, 3-trichloropropane (CAS Nos 3296-90-0, 75-52-5, and 96-18-4) in guppies (Poecilia reticulata) and medaka (Oryzias latipes) (waterborne studies). Natl Toxicol Program Tech Rep Ser 528: 1-190.
45. Newman LM, Wackett LP (1997) Trichloroethylene oxidation by purified toluene 2-monooxygenase: products, kinetics, and turnover-dependent inactivation. J Bacteriol 179: 90-96.
46. Oki DS, Giambelluca TW (1989) Groundwater contamination by nematicides: influence of recharge timing under pineapple crop. Water Res Bull 25: 285-294.
47. Oldenhuis R, Vink RLJM, Janssen DB (1989) Degradation of chlorinated aliphatic hydrocarbons by Methylosinus trichosporium OB3b expressing soluble methane monooxygenases. Appl Environ Microbiol 57: 2399-2402.
48. Pagan M, Cooper WJ, Joens JA (1998) Kinetic studies of the homogeneous abiotic reactions of several chlorinated aliphatic compounds in aqueous solution. Appl Geochem 13: 779-785.
49. Panke S, Sanchez-Romero JM, de Lorenzo V (1998) Engineering of quasi-natural Pseudomonas putida strains for toluene metabolism through an ortho-cleavage degradation pathway. Appl Environ Microbiol 64: 748-751.
50. Paul D, Pandey G, Pandey J, Jain R (2005) Accessing microbial diversity for bioremediation and environmental restoration. Trends Biotechnol 23: 135-142.
51. Pavlova M, Klvana M, Prokop Z, Chaloupkova R, Banas P, Otyepka M, Wade RC, Tsuda M, Nagata Y, Damborsky J (2009) Redesigning dehalogenase access tunnels as a strategy for degrading an anthropogenic substrate. Nat Chem Biol 5: 727-733.
52. Peijnenburg W, Eriksson L, de Groot A, Sjostrom M, Verboom H (1998) The kinetics of reductive dehalogenation of a set of halogenated aliphatic hydrocarbons in anaerobic sediment slurries. Environ Sci Pollut Res 5: 12-16.
53. Pezullo, J, Peterson R, Malot J (2005) Full scale remediation at a superfund site using in situ vacuum remediation and on-site regeneration case study-phase I. http://www. terravac. com/web/cases. htm#tyson. Accessed December 20, 2011.
54. Poelarends GJ, Vlieg JETV, Marchesi JR, Dos Santos LMF, Janssen DB (1999) Degradation of 1, 2-dibromoethane by Mycobacterium sp. strain GP1. J Bacteriol 181: 2050-2058.
55. Poelarends GJ, Zandstra M, Bosma T, Kulakov LA, Larkin MJ, Marchesi JR, Weightman AJ, Janssen DB (2000) Haloalkane utilizing Rhodococcus strains isolated from geographically distinct locations possess a highly conserved gene cluster encoding haloalkane catabolism. J Bacteriol 182: 2725-2731.
56. Rieger PG, Meier HM, Gerle M, Vogt U, Groth T, Knackmuss HJ (2002) Xenobiotics in the environment: present and future strategies to obviate the problem of biological persistence. J Biotechnol 94: 101-123.
57. Salter AJ, Tratynek PG, Johnson RL (2010) Degradation of 1, 2, 3-trichloropropane by zero-valent zinc: laboratory assessment for field application. Proceedings of the 7th International Conference on the Remediation of Chlorinated and Recalcitrant Compounds, 24-27 May 2010, Monterey, CA.
58. Salter-Blanc AJ, Tratnyek PG (2011) Effects of solution chemistry on the dechlorination of 1, 2, 3-trichloropropane by zero-valent zinc. Environ Sci Technol 45: 4073-4079.
59. Sarathy V, Salter AJ, Nurmi JT, O'Brien Johnson G, Johnson RL, Tratnyek PG (2010) Degradation of 1, 2, 3-trichloropropane (TCP): hydrolysis, elimination, and reduction by iron and zinc. Environ Sci Technol 44: 787-793.
60. Smidt H, de Vos W (2004) Anaerobic microbial dehalogenation. Annu Rev Microbiol 58: 43-73.
61. Stucki G, Thüer M (1995) Experiences of a large-scale application of 1, 2-dichloroethane degrading microorganisms for groundwater treatment. Environ Sci Technol 29: 2339-2345.
62. Tesoriero AJ, Lofflier FE, Leibscher H (2001) Fate and origin of 1, 2-dichloropropane in an unconfined shallow aquifer. Environ Sci Technol 35: 455-461.
63. Timmis K, Pieper D (1999) Bacteria designed for bioremediation. Trends Biotechnol 17: 201-204.
64. Tratnyek PG (2008) Fate and remediation of 1, 2, 3-trichloropropane. Proceedings of the 6th International Conference on the Remediation of Chlorinated and Recalcitrant Compounds, May 2008, Monterey, CA.
65. US EPA (2004) Non-confidential IUR Production Volume Information. http://www. epa. gov/iur/tools/data/2002-vol. html. Accessed December 22, 2011.
66. US EPA (2009) Toxicological review of 1, 2, 3-trichloropropane. EPA/635/R-08/010F.
67. US National Library of Medicine (2011) Toxicology Data Network, 1, 2, 3-trichloropropane. http://toxnet. nlm. nih. gov. Accessed December 24, 2011.
68. van den Wijngaard AJ, Janssen DB, Witholt B (1989) Degradation of epichlorohydrin and halohydrins by bacterial cultures isolated from fresh-water sediment. J Gen Microbiol 135: 2199-2208.
69. van den Wijngaard AJ, Wind RD, Janssen DB (1993) Kinetics of bacterial growth on chlorinated aliphatic compounds. Appl Environ Microbiol 59: 2041-2048.
70. van Hylckama Vlieg JET, Janssen DB (2001) Formation and detoxification of reactive intermediates in the metabolism of chlorinated ethenes. J Biotechnol 85: 81-102.
71. van Leeuwen JG, Wijma HJ, Floor RJ, van der Laan JM, Janssen DB (2012) Directed evolution strategies for enantiocomplementary haloalkane dehalogenases: from chemical waste to enantiopure building blocks. ChemBioChem 13: 137-148.
72. Weber GL, Sipes IG (1992) In vitro metabolism and bioactivation of 1, 2, 3-trichloropropane. Toxicol Appl Pharmacol 113: 152-158.
73. WHO (2003) Concise international chemical assessment document 56: 1, 2, 3-trichloropropane. http://www. who. int/ipcs/publications/cicad/en/cicad56. pdf. Accessed December 24, 2011.
74. Ya DK, Schoonhoven R, Ito N, Swenberg JA (1996) The effects of exposure route on DNA adduct formation and cellular proliferation by 1, 2, 3-trichloropropane. Toxicol Appl Pharmacol 140: 108-114.
75. Yamamoto K, Fukushima M, Kakutani N, Kuroda K (1997) Volatile organic compounds in urban rivers and their estuaries in Osaka, Japan. Environ Pollut 95: 135-143.
76. Yan J, Rash BA, Rainey FA, Moe WM (2009) Isolation of novel bacteria within the Chloroflexi capable of reductive dechlorination of 1, 2, 3-trichloropropane. Environ Microbiol 11: 833-843.
77. Yokota T, Omori T, Kodama T (1987) Purification and properties of haloalkane dehalogenase from Corynebacterium sp. strain m15-3. J Bacteriol 169: 4049-4054.
78. Yonetani R, Ikatsu H, Miyake-Nakayama C, Fujiwara E, Maehara Y, Miyoshi S, Matsuoka H, Shinoda S (2004) Isolation and characterization of a 1, 3-dichloro-2-propanol-degrading bacterium. J Health Sci 50: 605-612.