A mechanistic analysis of enzymatic degradation of organohalogen compounds

Bioscience, Biotechnology and Biochemistry

Volumn 75, Issue 2, 2011, Pages 189-198

  Kurihara, Tatsuo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

2 haloacrylate hydratase; 2 haloacrylate reductase; DL 2 haloacid dehalogenase; Fluoroacetate dehalogenase; L 2 haloacid dehalogenase

Indexed keywords

2-CHLOROACRYLATE; 2-HALOACRYLATE REDUCTASE; A-CARBON; ASPARTATE RESIDUE; ASYMMETRIC REDUCTION; CARBOXYLATE GROUPS; ENVIRONMENTAL TECHNOLOGIES; ENZYMATIC DEGRADATION; FLUOROACETATE; HALOACID DEHALOGENASE; HALOGEN ATOMS; HYDRATASE; MECHANISTIC ANALYSIS; ORGANOHALOGEN COMPOUNDS; PYRUVATES; REACTION CATALYZED; WATER MOLECULE;

ATOMS; CARBOXYLATION; CATALYSIS; CATALYSTS; CHEMICAL INDUSTRY; DEGRADATION; ENZYMES; ORGANIC COMPOUNDS; REDOX REACTIONS; SUBSTRATES;

HALOGEN COMPOUNDS;

ENZYME; HALOGEN; HYDROLASE; HYDROLYASE; ORGANIC COMPOUND; OXIDOREDUCTASE;

ANIMAL; CHEMISTRY; METABOLISM; REVIEW;

ANIMALS; ENZYMES; HALOGENS; HYDRO-LYASES; HYDROLASES; ORGANIC CHEMICALS; OXIDOREDUCTASES;

EID: 79952125741     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.100746     Document Type: Review

References (70)

1. Gribble GW, Chemosphere, 52, 289-297 (2003).
2. Janssen DB, Oppentocht JE, and Poelarends GJ, Curr. Opin. Biotechnol, 12, 254-258 (2001).
3. Janssen DB, Dinkla IJ, Poelarends GJ, and Terpstra P, Environ. Microbiol, 7, 1868-1882 (2005).
4. Nagata Y, Endo R, Ito M, Ohtsubo Y, and Tsuda M, Appl. Microbiol. Biotechnol, 76, 741-752 (2007).
5. Futagami T, Goto M, and Furukawa K, Chem. Rec, 8, 1-12 (2008).
6. Liu JQ, Kurihara T, Hasan AK, Nardi-Dei V, Koshikawa H, Esaki N, and Soda K, Appl. Environ. Microbiol, 60, 2389-2393 (1994).
7. Aravind L, Galperin MY, and Koonin EV, Trends Biochem. Set, 23, 127-129 (1998).
8. Toyoshima C, Nakasako M, Nomura H, and Ogawa H, Nature, 405, 647-655 (2000).
9. Hasan AKMQ, Takada H, Koshikawa H, Liu JQ, Kurihara T, Esaki N, and Soda K, Biosci. Biotechnol. Biochem., 58, 1599-1602 (1994).
10. Nardi-Dei V, Kurihara T, Okamura T, Liu JQ, Koshikawa H, Ozaki H, Terashima Y, Esaki N, and Soda K, Appl. Environ. Microbiol, 60, 3375-3380 (1994).
11. Liu JQ, Kurihara T, Esaki N, and Soda K, J. Biochem., 116, 248-249 (1994).
12. Liu JQ, Kurihara T, Nardi-Dei V, Okamura T, Esaki N, and Soda K, Biodegradation, 6, 223-227 (1995).
13. Kurihara T, Liu JQ, Nardi-Dei V, Koshikawa H, Esaki N, and Soda K, J. Biochem., 117, 1317-1322 (1995).
14. Liu JQ, Kurihara T, Miyagi M, Esaki N, and Soda K, J. Biol Chem., 270, 18309-18312 (1995).
15. Hisano T, Hata Y, Fujii T, Liu JQ, Kurihara T, Esaki N, and Soda K, Proteins, 24, 520-522 (1996).
16. Hisano T, Hata Y, Fujii T, Liu JQ, Kurihara T, Esaki N, and Soda K, J. Biol. Chem., 271, 20322-20330 (1996).
17. Liu JQ, Kurihara T, Miyagi M, Tsunasawa S, Nishihara M, Esaki N, and Soda K, J. Biol. Chem., 272, 3363-3368 (1997).
18. Li YF, Hata Y, Fujii T, Hisano T, Nishihara M, Kurihara T, and Esaki N, J. Biol. Chem., 273, 15035-15044 (1998).
19. Li YF, Hata Y, Fujii T, Kurihara T, and Esaki N, J. Biochem., 124, 20-22 (1998).
20. Ichiyama S, Kurihara T, Li YF, Kogure Y, Tsunasawa S, and Esaki N, J. Biol. Chem., 275, 40804-40809 (2000).
21. Li YF, Kurihara T, Ichiyama S, Miyagi M, Tsunasawa S, and Esaki N, J. Mol Cat. B: Enzymatic, 23, 337-345 (2003).
22. Nakamura T, Yamaguchi A, Kondo H, Watanabe H, Kurihara T, Esaki N, Hirono S, and Tanaka S, J. Comput. Chem., 30, 2625-2634 (2009).
23. Motosugi K, Esaki N, and Soda K, J. Bacterioi, 150, 522-527 (1982).
24. Park C, Kurihara T, Yoshimura T, Soda K, and Esaki N, J. Mol. Cat. B: Enzymatic, 23, 329-336 (2003).
25. Nardi-Dei V, Kurihara T, Park C, Esaki N, and Soda K, J. Bacterioi, 179, 4232-4238 (1997).
26. Nardi-Dei V, Kurihara T, Park C, Miyagi M, Tsunasawa S, Soda K, and Esaki N, J. Biol. Chem., 274, 20977-20981 (1999).
27. Verschueren KH, Seljee F, Rozeboom HJ, Kalk KH, and Dijkstra BW, Nature, 363, 693-698 (1993).
28. de Jong RM and Dijkstra BW, Curr. Opin. Struct. Biol, 13, 722-730 (2003).
29. Liu JQ, Kurihara T, Ichiyama S, Miyagi M, Tsunasawa S, Kawasaki H, Soda K, and Esaki N, J. Biol Chem., 273, 30897-30902 (1998).
30. Papajak E, Kwiecien RA, Rudzinski J, Sicinska D, Kaminski R, Szatkowski L, Kurihara T, Esaki N, and Paneth P, Biochemistry, 45, 6012-6017 (2006).
31. Schmidberger JW, Wilce JA, Weightman AJ, Whisstock JC, and Wilce MC, J. Mol Biol, 378, 284-294 (2008).
32. Omi R, Jitsumori K, Yamauchi T, Ichiyama S, Kurihara T, Esaki N, Kamiya N, Hirotsu K, and Miyahara I, Acta Crystallogr. F Struct. Biol Cryst. Commun., 63, 586-589 (2007).
33. Murphy CD, Schaffrath C, and O'Hagan D, Chemosphere, 52, 455-461 (2003).
34. Baron ML, Bothroyd CM, Rogers GI, Staffa A, and Rae ID, Phytochemistry, 26, 2293-2295 (1987).
35. Peters RA, Adv. Enzymol, 18, 113-159 (1957).
36. Proudfoot AT, Bradberry SM, and Vale JA, Toxicol Rev., 25, 213-219 (2006).
37. Lauble H, Kennedy MC, Emptage MH, Beinert H, and Stout CD, Proc. Natl Acad. Sci. USA, 93, 13699-13703 (1996).
38. Kawasaki H, Tone N, and Tonomura K, Agric. Biol Chem., 45, 29-34 (1992).
39. Kawasaki H, Tsuda K, Matsushita I, and Tonomura K, J. Gen. Microbiol, 138, 1317-1323 (1992).
40. Kurihara T, Yamauchi T, Ichiyama S, Takahata H, and Esaki N, J. Mol Cat. B: Enzymatic, 23, 347-355 (2003).
41. Goldman P, Science, 164, 1123-1130 (1969).
42. Gregg K, Hamdorf B, Henderson K, Kopecny J, and Wong C, Appl Environ. Microbiol, 64, 3496-3498 (1998).
43. Ichiyama S, Kurihara T, Miyagi M, Galkin A, Tsunasawa S, Kawasaki H, and Esaki N, J. Biochem., 131, 671-677 (2002).
44. Ichiyama S, Kurihara T, Kogure Y, Tsunasawa S, Kawasaki H, and Esaki N, Biochim. Biophys. Acta, 1698, 27-36 (2004).
45. Lewandowicz A, Sicinska D, Rudzinski J, Ichiyama S, Kurihara T, Esaki N, and Paneth P, J. Am. Chem. Soc, 123, 9192-9193 (2001).
46. Jitsumori K, Omi R, Kurihara T, Kurata A, Mihara H, Miyahara I, Hirotsu K, and Esaki N, J. Bacterioi, 191, 2630-2637 (2009).
47. Marek J, Vevodova J, Smatanova IK, Nagata Y, Svensson LA, Newman J, Takagi M, and Damborsky J, Biochemistry, 39, 14082-14086 (2000).
48. Newman J, Peat TS, Richard R, Kan L, Swanson PE, Affholter JA, Holmes IH, Schindler JF, Unkefer CJ, and Terwilliger TC, Biochemistry, 38, 16105-16114 (1999).
49. Kamachi T, Nakayama T, Shitamichi O, Jitsumori K, Kurihara T, Esaki N, and Yoshizawa K, Chemistry, 15, 7394-7403 (2009).
50. Banerjee R and Ragsdale SW, Annu. Rev. Biochem., 72, 209-247 (2003).
51. Poelarends GJ and Whitman CP, Bioorg. Chem., 32, 376-392 (2004).
52. de Jong RM, Bazzacco P, Poelarends GJ, Johnson WHJr, Kim YJ, Burks EA, Serrano H, Thunnissen AM, Whitman CP, and Dijkstra BW, J. Biol. Chem., 282, 2440-2449 (2007).
53. van der Waarde JJ, Kok R, and Janssen DB, Appl. Environ. Microbiol, 59, 528-535 (1993).
54. Marsden PJ and Casida JE, J. Agric. Food Chem., 30, 627-631 (1982).
55. Woolard FX, Moore RE, and Roller PP, Phytochemistry, 18, 617-620 (1979).
56. Kurata A, Kurihara T, Kamachi H, and Esaki N, Tetrahedron-Asymmetry, 15, 2837-2839 (2004).
57. Kurata A, Kurihara T, Kamachi H, and Esaki N, J. Biol. Chem., 280, 20286-20291 (2005).
58. Thorn JM, Barton JD, Dixon NE, Ollis DL, and Edwards KJ, J. Mol. Biol, 249, 785-799 (1995).
59. Edwards KJ, Barton JD, Rossjohn J, Thorn JM, Taylor GL, and Ollis DL, Arch. Biochem. Biophys., 328, 173-183 (1996).
60. Bossi RT, Negri A, Tedeschi G, and Mattevi A, Biochemistry, 41, 3018-3024 (2002).
61. Lancaster CR, Kroger A, Auer M, and Michel H, Nature, 402, 377-385 (1999).
62. Mowafy AM, Kurihara T, Kurata A, Uemura T, and Esaki N, Appl. Environ. Microbiol, 76, 6032-6037 (2010).
63. Haga T, Crosby KE, Schussler JR, Palmer CJ, Yoshii H, and Kimura F, "Aryloxyphenoxypropanoate Herbicides," eds. Kurihara N and Miyamoto J, John Wiley & Sons Ltd., Chichester, West Sussex, pp. 175-197 (1998).
64. Kurata A, Fujita M, Mowafy AM, Kamachi H, Kurihara T, and Esaki N, J. Biosci. Bioeng., 105, 429-431 (2008).
65. Smith DR, Doucette-Stamm LA, Deloughery C, Lee H, Dubois J, Aldredge T, Bashirzadeh R, Blakely D, Cook R, Gilbert K, Harrison D, Hoang L, Keagle P, Lumm W, Pothier B, Qiu D, Spadafora R, Vicaire R, Wang Y, Wierzbowski J, Gibson R, Jiwani N, Caruso A, Bush D, Safer H, Patwell D, Prabhakar S, Mcdougall S, Shimer G, Goyal A, Pietrokovski S, Church GM, Daniels CJ, Mao J, Rice P, Nolling J, and Reeve JN, J. Bacterioi, 179, 7135-7155 (1997).
66. Heim S, Kunkel A, Thauer RK, and Hedderich R, Eur. J. Biochem., 253, 292-299 (1998).
67. Thibodeaux CJ, Mansoorabadi SO, Kittleman W, Chang WC, and Liu HW, Biochemistry, 47, 2547-2558 (2008).
68. Unno H, Yamashita S, Ikeda Y, Sekiguchi SY, Yoshida N, Yoshimura T, Kusunoki M, Nakayama T, Nishino T, and Hemmi H, J. Biol. Chem., 284, 9160-9167 (2009).
69. Bornemann S, Nat. Prod. Rep., 19, 761-772 (2002).
70. Osborne A, Thorneley RN, Abell C, and Bornemann S, J. Biol. Chem., 275, 35825-35830 (2000).