Dehalogenases applied to industrial-scale biocatalysis

Current Opinion in Biotechnology

Volumn 10, Issue 4, 1999, Pages 365-369

  Swanson, Paul E ^a  

^a DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOIC ACID; DEHALOGENASE; ENZYME; HALIDE; LYASE; UNCLASSIFIED DRUG;

BIODEGRADATION; BIOTECHNOLOGY; CATALYSIS; DEHALOGENATION; INDUSTRY; PRIORITY JOURNAL; RECYCLING; REVIEW; WASTE MANAGEMENT;

EID: 0033179546     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(99)80066-4     Document Type: Article

References (38)

1. Neidleman SL, Giegert J: Halometabolites and their sources. In Biohalogenation: Principles, Basic Roles and Applications. Chichester: Ellis Horwood Ltd.; 1986:13-45.
2. Gschwend PM, MacFarlane JK, Newman KA: Volatile halogenated organic compounds released to seawater from temperate marine macroalgae. Science 1985, 227:1033-1035.
3. Weissermel K, Arpe HJ: Industrial Organic Chemistry, Edn 3. New York: VCH Publishers, Inc.; 1997.
4. Pries F, Van der Ploeg JR, Dolfing J, Janssen DB: Degradation of halogenated aliphatic compounds: The role of adaptation. FEMS Microbiol Rev 1994, 15:279-295.
5. Slater JH, Bull AT, Hardman DJ: Microbial dehalogenation. Biodegradation 1995, 6:181-189.
6. Slater JH: Microbial dehalogenation of haloaliphatic compounds. In Biochemistry of Microbial Degradation. Edited by Ratledge C. Dordrecht: Kluwer Academic Publishers; 1994:379-421.
7. Slater JH, Bull AT, Hardman DJ: Microbial dehalogenation of halogenated alkanoic acids, alcohols and alkanes. Adv Microbiol Physiol 1997, 38:133-176.
8. Fantroussi SE, Naveau H, Agathos SN: Anaerobic dechlorinating bacteria. Biotechnol Prog 1998, 14:167-188.
9. Fetzner S, Lingens F: Bacterial dehalogenases: Biochemistry, genetics, and biotechnological applications. Microbiol Rev 1994, 58:641-685.
10. Van Agteren MH, Kenning S, Janssen DB: Handbook on Biodegradation and Biological Treatment of Hazardous Organic Compounds. Dordrecht: Kluwer Academic Publishers; 1998.
11. Janssen DB, Pries F, Van der Ploeg JR: Genetics and biochemistry of dehalogenating enzymes. Annu Rev Microbiol 1994, 48:163-191.
12. Uhlig H, Goldstein WE, Hagen HA, Poldermans B, Reimerdes EH, Leuchtenberger W, Waldman H, Grabowski S, Simon ES, Whitesides GM: Industrial uses of enzymes. In Enzymes in Industry: Production and Applications. Edited by Gerhartz W. New York: VCH Publishers; 1990:77-149.
13. Kasai N, Suzuki T, Furukawa Y: Chiral C3 epoxides and halohydrins: Their preparation and synthetic application. J Mol Catal B: Enzymatic 1998, 4:237-252.
14. Kasai N, Suzuki T: Development of microbial production of optically active C3 synthetic units. Seibutsu Kogaku Kaishi 1997, 75:255-275.
15. Suzuki T, Kasai N, Minamiura N: A novel generation of optically active 1,2-diols from the racemates by using halohydrin-dehydrodehalogenase. Tetrahedron Asymmetry 1994, 5:239-246.
16. Suzuki T, Idogaki H, Kasai N: Production of (S)-4-chloro-3-hydroxybutyronitrile using microbial resolution. Biorg Med Chem Lett 1996, 6:2581-2584.
17. Yu F, Nakamura T, Mizunashi W, Watanabe I: Cloning of two halohydrin hydrogen-halide-lyase genes of Corynebacterium sp. strain N-1074 and structural comparison of the genes and gene products. Biosci Biotechnol Biochem 1994, 58:1451 -1457.
18. Nakamura T, Nagasawa T, Yu F, Watanabe I, Yamada H: Characterization of a novel enantioselective halohydrin hydrogenhalide lyase. Appl Environ Microbiol 1994, 60:1297-1301.
19. Nakamura T, Yu F, Mizunashi W, Watanabe I: Production of (R)-3-chloro-1,2-propanediolchloro-1,2-propanediol from prochiral 1,3-dichloro-2-propanol by Corynebacterium sp. strain N-1074. Appl Environ Microbiol 1993, 59:227-230.
20. Nakamura T, Nagasawa T, Yu F, Watanabe I, Yamada H: Purification and characterization of two epoxide-hydrolases from Corynebacterium sp. strain N-1074. Appl Environ Microbiol 1994, 60:4630-4633.
21. Nakamura T, Nagasawa T, Yu F, Watanabe I, Yamada H: A new enzymatic synthesis of (R)-gamma-chloro-beta-hydroxynitrile. Tetrahedron 1994, 50:11821-11826.
22. Assis HMS, Sallis PJ, Bull AT, Hardman DJ: Biochemical characterization of a haloalcohol dehalogenase from Arthrobacter erithii H10a. Enzyme Microbiol Technol 1998, 22:568-574.
23. Assis HMS, Bull AT, Hardman DJ: Synthesis of chiral epihalohydrins using haloalcohol dehalogenase A from Arthrobacter erithii H10a. Enzyme Microbiol Technol 1998, 22:545-551. An up to date approach to using haloalcohol hydrogen-halide lyase enzymes to make chiral epichlorohydrin from 13DCP.
24. Taylor SC: S-2-chloropropionic acid by biotransformation. In Opportunities in Biotransformations. Edited by Copping LG, Martin RE, Pickett JA, Bucke C, Bunch AW. New York: Elsevier Applied Science Publishers; 1990:170-176.
25. Li YF, Hata Y, Fujii T, Kurihara T, Esaki N: X-ray structure of a reaction intermediate of L-2-haloacid dehalogenase with L-2-chloropropionamide. J Biochem 1998, 124:20-22.
26. Li YF, Hata Y, Fujii T, Hisano T, Nishihara M, Kurihara T, Esaki N: Crystal structures of reaction intermediates of L-2-haloacid dehalogenase and implications for the reaction mechanism. J Biol Chem 1998, 278:15035-15044.
27. Lui JQ, Kurihara T, Hasan AK, Nardi-Diev V, Koshikawa H, Esaki N, Soda K: Purification and characterization of thermostable and nonthermostable 2-haloacid dehalogenases with different stereospecificities from Pseudomonas sp strain YL. Appl Environ Microbiol 1994, 60:2389-2393.
28. Diez A, Prieto MI, Alvarez MJ, Bautista JM, Puyet A, Garrido-Pertierra A: Purification and properties of a igh-affinity L-2-haloacid dehalogenase from Azotobacter sp. strain RC26. Lett Applied Microbiol 1996, 23:279-282.
29. Hasan AKMQ, Takada H, Esaki N, Soda K: Catalytic action of L-2-halo acid dehalogenase on long-chain L-2-haloalkanoic acids in organic solvents. Biotechnol Bioeng 1991, 38:1114-1117.
30. Vyazmensky M, Geresh S: Substrate specificity and product stereochemistry in the dehalogenation of 2-haloacids with the crude enzyme preparation from Pseudomonas putida. Enzyme Microbiol Technol 1998, 22:323-328.
31. Janssen DB, Scheper A, Dijkhuizen L, Witholt B: Degradation of halogenated aliphatic compounds by Xanthobacter autotrophicus GJ10. Appl Environ Microbiol 1985, 49:673-677.
32. Damborsky J, Nyandoroh MG, Nemec M, Holoubek I, Bull AT, Hardman DJ: Some biochemical properties and the classification of a range of bacterial haloalkane dehalogenases. Biotechnol Appl Biochem 1997, 26:19-25.
33. Nagata Y, Miyauchi K, Damborsky J, Manova K, ANsorgova A, Takagi M: Purification and characterization of a haloalkane dehalogenase of a new substrate class from a γ-hexa chloro cyclo hexane-degrading bacterium, Sphingomonas paucimobilis UT26. Appl Environ Microbiol 1997, 63:3707-3710.
34. Krooshof GH, Ridder IS, Tepper AWJW, Vos GJ, Rozeboom HJ, Kalk KH, Dijkstra BW, Janssen DB: Kinetic analysis and x-ray structure of haloalkane dehalogenase with a modified halide-binding site. Biochemistry 1998, 37:15013-15023. This paper and [36•] describe recent site-directed mutagenesis studies focused on understanding catalytic mechanism and substrate range of the Xanthobacter haloalkane dehalogenase.
35. Pries F, Kingma J, Pentenga M, Van Pouderoyen G, Jeronimus-Stratingh MJ, Bruins AP, Janssen DB: Site-directed mutagenesis and oxygen isotope incorporation studies of the nucleophilic aspartate of haloalkane dehalogenase. Biochemistry 1994, 33:1242-1247.
36. Holloway P, Knoke KL, Trevors JT, Lee H: Alteration of the substrate range of haloalkane dehalogenase by site-directed mutagenesis. Biotechnol Bioeng 1998, 59:520-523. See annotation to [34•].
37. Swanson PE: Development of dehalogenase enzymes for industrial scale biocatalysis. In IBC World Congress on Enzyme Technologies: 1999 10-12 March 1999; San Franciso, CA.
38. Kauffmann C, Mandelbaum RT: Entrapment atrazine chlorohydrolase in sol-gel glass matrix. J Biotechnol 1998, 62:169-176.