Synthesis of chiral epihalohydrins using haloalcohol dehalogenase A from Arthrobacter erithii H10a

Enzyme and Microbial Technology

Volumn 22, Issue 7, 1998, Pages 545-551

  Assis, H M S ^a   Bull, A T ^a   Hardman, D J ^a  

^a UNIVERSITY OF KENT   (United Kingdom)

Author keywords

Arthrobacter erithii H10a; Enantioselective dehalogenation; Enantioselective halogenation; Haloalcohol dehalogenase; Optically active epihalohydrins

Indexed keywords

ALCOHOLS; BACTERIA; CHLORINATION; CHLORINE COMPOUNDS; DEHALOGENATION; ENZYMES; SUBSTRATES;

ENANTIOSELECTIVE HALOGENATION; EPICHLOROHYDRIN; HALOALCOHOLS DEHALOGENASE; PROPANOL;

BIOSYNTHESIS;

BACTERIAL ENZYME; CHLORIDE; HALOGEN; PROPANOL;

ARTHROBACTER; ARTICLE; DEHALOGENATION; NONHUMAN;

ARTHROBACTER ERITHII;

EID: 0032524179     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(97)00255-X     Document Type: Article

References (21)

1. Kasai N., Tsujimura K., Unoura K., Suzuki T. Isolation of (S)-2,3-dichloro-1-propanol assimilating bacterium, its characterization, and its use in preparation of (R)-2,3-dichloro-1-propanol and (S)-epichlorohydrin. J. Ind. Microbiol. 10:1992;37-43.
2. Baldwing J.J., Raab A.W., Mensler K., Arison B.H., McClure D.E. Synthesis of (R)- and (S)-epichlorohydrin. J. Org. Chem. 43:1978;4876-4878.
3. Katsuki T., Sharpless B.K. The first practical method for asymmetric epoxidation. J. Am. Chem. Soc. 102:1980;5974-5976.
4. Iruchijima S., Keiyu A., Kojima N. Asymmetric hydrolysis of (±)-1-acetoxy-2,3-dichloropropane with enzymes and microorganisms. Agric. Biol. Chem. 46:1982;1593-1597.
5. Weijers C.A.G.M., deBont J.A.M. Enantioselective degradation of 1,2-epoxyalkanes by Nocardia H8. Enzyml. Microb. Technol. 13:1991;306-308.
6. Habets-Crutzen A.Q.H., Carlier S.J.N., deBont J.A.M., Wistuba D., Schurig V., Hartmans S., Tramper J. Stereospecific formation of 1,2-epoxypropane and 1,2-epoxybutane and 1-chloro-2,3-epoxypropane by alkene-utilizing bacteria. Enzyml. Microb. Technol. 7:1985;17-21.
7. Taylor, S. C. D-2-Haloalkanoic acid halidohydrolase. U.S. Patent 4,758,518; July 1988.
8. Kasai N., Tsujimura K., Unoura K., Suzuki T. Degradation of 2,3-dichloro-1-propanol by a Pseudomonas sp. Agric. Biol. Chem. 54:1990;3185-3190.
9. Suzuki T., Kasai N. A novel method for the generation of (R)- and (S)-3-chloro-1,2-propanediol by stereospecific dehalogenating bacteria and their use in the preparation of (R)- and (S)-glycidol. Bioorg. Med. Chem. Lett. 1:1991;343-346.
10. Suzuki T., Kasai N., Yamamoto R., Minamiura N. Isolation of a bacterium assimilating (R)-3-chloro-1,2-propanediol and production of (S)-3-chloro-1,2-propanediol using microbial resolution. J. Ferm. Bioeng. 73:1992;443-448.
11. Nakamura T., Yu F., Mizunashi W., Watanabe I. Production of (R)-3-chloro-1,2-propanediol from prochiral 1,3-dichloro-2-propanol by Corynebacterium sp. strain N-1074. Appl. Environ. Microbiol. 59:1993;227-230.
12. Bull, A. T., Hardman, D. J., Sallis, P. J., and Stubbs, B. M. Dehalogenation of organohalogen-containing compounds. U.S. patent P10504.SO1; April 1992.
13. Assis H.M.S., Sallis P.J., Bull A.T., Hardman D.J. Biochemical characterization of a haloalcohol dehalogenase from Arthrobacter erithii H10a. Enzyme Microb. Technol. 22:1998;568-574.
14. Hardman D.J., Slater J.H. Dehalogenases in soil bacteria. J. Gen. Microbiol. 123:1981;117-128.
15. Sedmak J.J., Grossberg S.E. A rapid, sensitive and versatile assay for protein using Commassie Brilliant Blue G250. Anal. Biochem. 79:1977;544-552.
16. Kasai N., Tsujimura K., Unoura K., Suzuki T. Preparation of (S)-2,3-dichloro-1-propanol by Pseudomonas sp. and its use in the synthesis of (R)-epichlorohydrin. J. Ind. Microb. 9:1992;97-101.
17. Nakamura T., Nagasawa T., Yu F., Watanabe I., Yamada H. Characterization of a novel enantioselective halohydrin hydrogen-halide-lyase. Appl. Env. Microbiol. 60:1994;1297-1301.
18. Nakamura T., Nagasawa T., Yu F., Watanabe I., Yamada H. Resolution and some properties of enzymes involved in enantioselective transformation of 1,3-dichloro-2-propanol to (R)-3-chloro-1,2-propanediol by Corynebacterium sp. strain N-1074. J. Bacteriol. 174:1992;7613-7619.
19. Nakamura T., Nagasawa T., Yu F., Watanabe I., Yamada H. A new catalytic function of halohydrin hydrogen-halide-lyase, synthesis of β-hydroxynitriles from epoxides and cyanide. Biochem. Biophys. Res. Comm. 180:1991;124-130.
20. Wandel U., Konigsberger K., Griengl H. Enantioselectivity of epoxide formation from halohydrins by means of Flavobacterium rigense. Biocatalysis. 10:1994;159-168.
21. Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem. Rev. 92:1992;1071-1140.