Synthesis of enantiopure epoxides through biocatalytic approaches

Annual Review of Microbiology

Volumn 51, Issue , 1997, Pages 491-525

  Archelas, A ^a   Furstoss, R ^a  

^a ETABLISSEMENT FRANÇAIS DU SANG   (France)

Author keywords

Biotransformations; Chiral epoxides; Epoxidation; Epoxide hydrolysis

Indexed keywords

EPOXIDE; MICROBIAL ENZYME; OXYGENASE; UNSPECIFIC MONOOXYGENASE;

BIOTRANSFORMATION; CATALYSIS; CHIRALITY; ENANTIOMER; ENZYME ANALYSIS; EPOXIDATION; NONHUMAN; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

BIOCHEMISTRY; EPOXY COMPOUNDS; HEME; HYDROCARBONS, HALOGENATED; HYDROLASES; METHANE; MIXED FUNCTION OXYGENASES; OXIDOREDUCTASES; OXYGENASES; PEROXIDASES;

EID: 0030798603     PISSN: 00664227     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.micro.51.1.491     Document Type: Review

References (175)

1. Abbott BJ, Hou CT. 1973. Oxidation of 1-alkenes to 1,2-epoxyalkanes by Pseudomonas oleovorans. Appl. Microbiol. 26:86-91
2. Agase Agrochemicals. 1995. Jpn. Patent No. Jp 07099-993
3. Allain EJ, Hager LP. 1993. Highly enantioselective epoxidation of disubstituted alkenes with hydrogen peroxide catalysed by chloroperoxydase. J. Am. Chem. Soc. 115:4415-16
4. Allen RH, Jakoby WB. 1969. Tartaricacid metabolism. IX. Synthesis with tartrate epoxidase. J. Biol. Chem. 244:2078-84
5. Arand M, Wagner H, Oesch F. 1996. Asp333, Asp495, and His523 form the catalytic triad of rat soluble epoxide hydrolase. J. Biol. Chem. 271:4223-29
6. Archelas A, Delbecque JP, Furstoss R. 1993. Microbiological transformations. 30. Enantioselective hydrolysis of racemic epoxides: the synthesis of enantiopure insect juvenile hormone analogs (Bower's compound). Tetrahedron Asymmetry 4:2445-46
7. Archelas A, Furstoss R. 1992. Synthesis of optically pure pityol - a pheromone of the bark beetle Pityophthorus pityographus - using a chemoenzymatic route. Tetrahedron Lett. 33:5241-42
8. Archelas A, Hartmans S, Tramper J. 1988. Stereoselective epoxydation of 4-bromo-1-butene and 3-butene-1-ol with three alkene-utilizing bacteria. Biocatalysis 1:283-92
9. Avignon-Tropis M, Treilhou M, Pougny JR, Frechard-Ortuno I, Linstrumelle G. 1991. Total synthesis of (+)-leukotriene B4 methyl ester and its 5-epimer from (R)-glycidol. Tetrahedron 47:7279-86
10. Bangcharoenpaurpong O, Champion PM, Hall KS, Hager LP. 1986. Resonance raman studies of isotopically labeled chloroperoxidase. Biochemistry 25: 2374-78
11. Bellucci G, Berti G, Catelani G, Mastrorilli E. 1981. Unusual steric course of the epoxide hydrolase catalyzed hydrolysis of ±-3,4-epoxytetrahydropyran. A case of complete stereo-convergence. J. Org. Chem. 46:5148-50
12. Bellucci G, Chiappe C, Cordoni A. 1996. Enantioconvergent transformation of racemic cis-β-alkyl substituted styrene oxides to (R,R) threo diol by microsomal epoxide hydrolase catalysed hydrolysis. Tetrahedron Asymmetry 7:197-202
13. Bellucci G, Chiappe C, Cordoni A, Marioni F. 1994. Different enantioselectivity and regioselectivity of the cytosolic and microsomal epoxide hydrolase catalyzed hydrolysis of simple phenyl substituted epoxides. Tetrahedron Lett. 35:4219-22
14. Bellucci G, Chiappe C, Ingrosso G, Rosini C. 1995. Kinetic resolution by epoxide hydrolase catalyzed hydrolysis of racemic methyl substituted methylenecy-clohexene oxides. Tetrahedron Asymmetry 6:1911-18
15. Berti G. 1986. Enantio- and diastereoselectiviy of microsomal epoxide hydrolase: potential applications to the preparation of non-racemic epoxides and diols. In Enzymes as Catalysts in Organic Synthesis, ed. MP Schneider, 178:349-54. Dordrecht, Holland: D. Reidel
16. Besse P, Renard MF, Veschambre H. 1994. Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane. Tetrahedron Asymmetry 5: 1249-68
17. Besse P, Veschambre H. 1993. Chemoenzymatic synthesis of "α-bichiral" synthons. Application to the preparation of chiral epoxides. Tetrahedron Asymmetry 4:1271-85
18. Besse P, Veschambre H. 1994. Chemical and biological synthesis of chiral epoxides. Tetrahedron 50:8885-927
19. Blanke SR, Yi S, Hager LP. 1989. Development of semi-continuous and continuous-flow bioreactors for the high-level production of chloroperoxidase. Biotechnol. Lett. 11:769-74
20. Blee E, Schuber F. 1995. Stereocontrolled hydrolysis of the linoleic acid monoepoxide regioisomers catalyzed by soybean epoxide hydrolase. Eur. J. Biochem. 230:229-34
21. Borhan B, Jones DA, Pinot F, Grant DF, Kurth MJ, Hammock BD. 1995. Mechanism of soluble epoxide hydrolase. Formation of an α-hydroxy ester-enzyme intermediate through Asp333. J. Biol. Chem. 270:26923-30
22. Brink LES, Tramper J. 1985. Optimization of organic solvent in multiphase biocatalysis. Biotechnol. Bioeng. 27:1258-69
23. Brown HC, Pai GG. 1983. Asymmetric reduction of prochiral α-halo ketones with B-3-pinanyl-9-borabicyclo[3.3.1]-nonane. J. Org. Chem. 48:1784-86
24. Gabon O, Buisson D, Larcheveque M, Azerad R. 1995. The microbial reduction of 2-chloro-3-oxoesters. Tetrahedron Asymmetry 6:2199-210
25. Cabon O, Buisson D, Larcheveque M, Azerad R. 1995. Stereospecific preparation of glycidic esters from 2-chloro-3-hydroxyesters. Application to the synthesis of (2R,3S)-3-phenylisoserine. Tetrahedron Asymmetry 6:2211-18
26. Castro CE, Bartnicki EW. 1968. Biohalogenation. Epoxidation of halohydrins, epoxide opening, and transhalogenation. Biochemistry 7:3213-18
27. Cerniglia CE, Yang SK. 1984. Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans. Appl. Environ. Microbiol. 47:119-24
28. Chartrain M, Senanayake CH, Rosazza JPN, Zhang J. 1996. Int. Patent No. WO96/12818
29. Chen X-J, Archelas A, Furstoss R. 1993. Microbial transformations. 27. The first examples for preparative-scale enantioselective or diastereoselective epoxides hydrolyses using microorganisms. An unequivocal access to all four bisabolol stereoisomers. J. Org. Chem. 58:5528-32
30. Colonna S, Gaggero N, Casella L, Carrea G, Pasta P. 1993. Enantioselective epoxidation of styrene derivatives by chloroperoxidase catalysis. Tetrahedron Asymmetry 4:1325-30
31. Coote SJ, Davies SG, Middlemiss D, Naylor A. 1989. Enantiospecific synthesis of (+)-(R)-6,7-dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline from (+)-(S)-2-methylamino-1 -phenylethanol (halostachine). J. Chem. Soc. Perkin Trans. 1:2223-28
32. De Bont JAM. 1993. Bioformation of optically pure epoxides. Tetrahedron Asymmetry 4:1331-40
33. De Bont JAM, Attwood MM, Primrose SB, Harder W. 1979. Epoxidation of short chain alkenes in Mycobacterium E20: the involvement of a specific monooxygenase. Fems Microbiol. Lett. 6:183-88
34. De Bont JAM, van Dijken JP, van Ginkel KG. 1982. The metabolism of 1,2-propanediol by the propylene oxide utilizing bacterium Nocardia A60. Biochim. Biophys. Acta 714:465-70
35. Den Wijngaard AJ, Reuvekamp PTW, Janssen DB. 1991. Purification and characterisation of haloalcohol dehalogenase from Arthrobacter sp. strain AD2. J. Bacteriol. 173:124-29
36. Dexter AF, Hager LP. 1995. Transient heme N-alkylation of chloroperoxidase by terminal alkenes and alkynes. J. Am. Chem. Soc. 117:817-18
37. Dexter AF, Lakner FJ, Campbell RA, Hager LP. 1995. Highly enantioselective epoxidation of 1,1-disubstituted alkenes catalyzed by chloroperoxidase. J. Am. Chem. Sm. 117:6412-13
38. Elks J, Ganellin CR. 1990. Diltiazem in Dictionary of Drugs, p. 426. London: Chapmann & Hall
39. Escoffier B, Prome JC. 1989. Conversion of steroids and triterpenes by Mycobacteria - stereospecific hydrolysis of steroidal spiro-3-ξ-oxiranes by Mycobacterium aurum. Bioorg. Chem. 17:53-63
40. Faber K, Mischitz M, Kroutil W. 1996. Microbial epoxide hydrolases. Acta Chem. Scand. 50:249-58
41. Fedresel HF. 1993. Drug Chirality-Scale-Up, Manufacturing, and Control. A Comprehensive Review of All the Things You Have to Consider When Making the Drug You Want, ed. I Ojima, 23:24-33. New York: Verlag Chemie
42. Ferraboschi P, Casati S, Grisenti P, Santaniello E. 1994. Selective enzymatic transformations of itaconic acid derivatives: an access to potentially useful building blocks. Tetrahedron 50:3251-58
43. Ferraboschi P, Grisenti P, Manzocchi A, Santaniello E. 1994. Regio- and enantioselectivity of Pseudomonas cepacia lipase in the transesterification of 2-substituted-1,4-butanediols. Tetrahedron Asymmetry 5:691-98
44. Fetzner S, Lingens F. 1994. Bacterial dehalogenases: biochemistry, genetics and biotechnological applications. Microbiol. Rev. 58:641-85
45. Fox BG, Borneman JG, Wackett LP, Lipscomb JD. 1990. Haloalkene oxidation by the soluble methane monooxygenase from Methylosinus trichosporium OB3b: mechanistic and environmental implications. Biochemistry 29:6419-27
46. Furuhashi K. 1989. Jpn. Patent No. 01075479A
47. Furuhashi K, Shintani M, Takagi M. 1986. Effects of solvents on the production of epoxides by Nocardia corallina B-276. Appl. Microbiol. Biotechnol. 23:218-23
48. Geerlof A, Jongejan JA, van Dooren TJGM, Raemakers-Franken PC, den Tweel WJJ, Duine JA. 1994. Factors relevant to the production of (R)-(+)-glycidol (2,3-epoxy-1-propanol) from racemic glycidol by enantioselective oxidation with Acetobacter pasteurianus atcc 12874. Enzyme Microb. Technol. 16:1059-66
49. Geigert J, Lee TD, Dalietos DJ, Hirano DS, Neidleman SL. 1986. Epoxidation of alkenes by chloroperoxidase catalysis. Biochem. Biophys. Res. Commun. 136:778-82
50. Geigert J, Neidleman SL, Dalietos DJ, DeWitt SK. 1983. Haloperoxidases: enzymatic synthesis of α,β-halohydrins from gaseous alkenes. Appl. Environ. Microbiol. 45:366-74
51. Gentile A, Giordano C, Fuganti C, Ghirotto L, Servi S. 1992. The enzymatic preparation of (2R,3S) phenyl glycidic acid esters. J. Org. Chem. 57:6635-37
52. Gou DM, Liu YC, Chen CS. 1993. A practical chemoenzymatic synthesis of the taxol C-13 side chain N-benzoyl-(2R,3S)-3-phenylisoserine. J. Org. Chem. 58:1287-89
53. Griffin BW. 1983. Mechanism of halide-stimulated activity of chloroperoxidase evidence for enzymatic formation of free hypohalous acid. Biochem. Biophys. Res. Commun. 116:873-79
54. Guengerich FP. 1991. Reactions and significance of cytochrome P-450 enzymes. J. Biol. Chem. 266:10019-22
55. Habets-Crutzen AQH, Brink LES, Van Ginkel CG, de Boni JAM, Tramper J. 1984. Production of epoxides from gaseous alkenes by resting-cell suspensions and immobilized cells of alkene-utilizing bacteria. Appl. Microbiol. Biotechnol. 20:245-50
56. Habets-Crutzen AQH, Carlier SJN, de Bont JAM, Wistuba D, Schurig V, et al. 1985. Stereospecific formation of 1,2-epoxypropane, 1,2-epoxybutane and 1-chloro-2,3-epoxypropane by alkene-utilizing bacteria. Enzyme Microb. Technol. 7:17-21
57. Hager LP et al. 1994. US Patent No. 5358860
58. Hager LP, Morris DR, Brown FS, Eberwein H. 1966. Chloroperoxidase. Utilisation of halogen anions. J. Biol. Chem. 241:1769-77
59. Hammock BD, Grant DF, Storms DH. 1996. Epoxide hydrolases. In Comprehensive Toxicology, ed. I Sipes, C McQueen, A Gandolfi, Ch 18.3. Oxford: Pergamon
60. Hartmann GR, Frear DS. 1963. Enzymatic hydration of cis-9,10-epoxyoctadecanoic acid by cell-free extracts of germinating flax rust uredospores. Biochem. Biophys. Res. Commun. 10:366-72
61. Hawkins DR, ed. 1994. A Survey of the Biotransformations of Drugs and Chemicals in Animals, Vol. 1-5. Cambridge: Royal Soc. Chem.
62. Hechtberger P, Wirnsberger G, Mischitz M, Kiempier N, Faber K. 1993. Asymmetric hydrolysis of epoxides using an immobilized enzyme preparation from Rhodococcus sp. Tetrahedron Asymmetry 4:1161-64
63. Holland HL. 1992. Organic Synthesis with Oxidative Enzymes, ed. HL Holland, pp. 55-199. New York: VCH
64. Hou CT, Patel RN, Laskin AI. 1980. US Patent No. 4368267
65. Hou CT, Patel RN, Laskin AI, Barnabe N. 1979. Microbial oxidation of gaseous hydrocarbons: epoxidation of C2 to C4 n-alkenes by methyltotrophic bacteria. Appl. Environ. Microbiol. 38:127-34
66. Huylshof LA, Hendrik J. 1989. Eur. Patent No. 0343714AI
67. Imai K, Marumo S, Mori K. 1974. Derivation of (+)- and (-)-C17-juvenile hormone from its raceme alcohol derivative via fungal metabolism. J. Am. Chem. Soc. 96:5925-27
68. Imuta M, Kawai KI, Ziffer H. 1980. Product stereospecificity in the microbial reduction of α-haloaryl ketones. J. Org. Chem. 45:3352-55
69. Itoh M, Kusaka M, Hirota T, Nomura A. 1995. Microbial production of antibiotic fosfomycin by a stereoselective epoxidation and its formation mechanism. Appl. Microbial. Biotechnol. 43:394-401
70. Jacobs MH, van den Wijngaard AJ, Pentenga M, Janssen DB. 1991. Characterization of the epoxide hydrolase from an epichlorohydrin-degrading Pseudomonas sp, Eur. J. Biochem. 202:1217-22
71. Johnstone SL, Phillips GT, Robertson BW, Watts PD, Bertola MA, et al. 1987. Stereoselective synthesis of S-(-)-β-blockers via microhially produced epoxide intermediates. In Biocatalysis in Organic Media, ed. C Laane, J Tramper, MD Lilly, pp. 387-92. Elsevier: Amsterdam
72. Kamal A, Damayanthi Y, Rao MV. 1992. Stereoselective synthesis of (5)-propanol amines: lipase catalyzed opening of epoxides with 2-propylamine. Tetrahedron Asymmetry 3:1361-64
73. Kamal A, Rao AB, Rao MV. 1992. Stereoselective synthesis of (5)-propanol amines: liver microsomes mediated opening of epoxides with arylamines. Tetrahedron Lett. 33:4077-80
74. Kasai N, Tsujimura K, Unoura K, Suzuki T. 1992. Preparation of (S)-2,3-dichloro-1-propanol by Pseudomonas sp. and its use in the synthesis of (R)-epichlorhydrin. J. Indust. Microbiol. 9:97-101
75. Katsuki T. 1995. Catalytic asymmetric oxidations using optically active (salen)manganese(III) complexes as catalysts. Coord. Chem. Rev. 140:189-214
76. Katsuki T. 1995. Mn-Salen catalyzed asymmetric oxidation of simple olefins and Sulfides. J. Synth. Org. Chem. Jpn. 53:940-51
77. Kloosterman M, Elferink VHM, van Iersel J, Roskam JH, Meijer EM, et al. 1988. Lipase in the preparation of β-blockers. Trends Biotechnol. 6:251-56
78. Klunder JM, Ko SY, Sharpless KB. 1986. Asymmetric epoxidation of allyl alcohol: efficient routes to homochiral β-adrenergic blocking agents. J. Org. Chem. 51:3710-12
79. Knehr M, Thomas H, Arand M, Gebel T, Zeller HD, Oesch F. 1993. Isolation and characterization of a cDNA encoding rat liver cytosolic epoxide hydrolase and its functional expression in Escherichia coli. J. Biol. Chem. 268:17623-27
80. Kolattukudy PE, Brown L. 1975. Fate of naturally occurring epoxy acids : a soluble epoxide hydrase, which catalyzes cis hydration, from Fusarium solani pisi. Arch. Biochem. Biophys. 166:599-607
81. Kolb HC, Sharpless KB. 1992. A simplified procedure for the stereospecific transformation of 2-diols into epoxides. Tetrahedron 48:10515-30
82. Kolb HC, van Nieuwenhze MS, Sharpless KB. 1994. Catalytic asymmetric dihydroxylation. Chem. Rev. 94:2483-547
83. Krenn BE, Plat H, Wever R. 1988. Purification and some characteristics of a non-haem bromoperoxidase from Streptomyces aureofaciens. Biochim. Biophys. Ada 952:255-60
84. Lacourciere GM, Armstrong RN. 1993. The catalytic mechanism of microsomal epoxide hydrolase involves an ester intermediate. J. Am. Chem. Soc. 115:10466-67
85. Ladner WE, Whitesides GM. 1984. Lipase-catalyzed hydrolysis as a route to esters of chiral epoxy alcohols. J. Am. Chem. Soc. 106:7250-51
86. Lakner FJ, Hager LP. 1996. Chloroperoxidase as enantioselective epoxidation cata lyst: an efficient synthesis of (R)-(-)-mevanolactone. J. Org. Chem. 61:3923-25
87. Leak DJ, Dalton H. 1987. Studies on the regioselectivity and stereoselectivity of the soluble methane monooxygenase from Methylococcus capsulatus (bath). Biocatalysis 1:23-36
88. Levinger DC, Stevenson JA, Wong LL. 1995. The catalytic activity of human myoglobin is enhanced by a single active site mutation: F42Y. J. Chem. Soc., Chem. Commun. 22:2305-6
89. Libby R D, Thomas JA, Kaiser LW, Hager LP. 1982. Chloroperoxidase halogenation reactions. Chemical versus enzymic halogenating intermediates. J. Biol. Chem. 257:5030-37
90. 18O-labeling studies. Tetrahedron 51:10845-56
91. Lohray BB. 1992. Cyclic sulfites and cyclic sulfates: epoxide like synthons. Synthesis 11:1035-52
92. Lu AYH, West SB. 1980. Multiplicity of mammalian microsomal cytochromes P-450. Pharmacol. Rev. 31:277-95
93. Machado SS, Wandel U, Straathof AJJ, Jongejan JA, Duine JA. 1996. Production of (R)-glycidol by Acetobacter pasteurianus. Presented at Int. Conf. Biotech. Ind. Prod. Fine Chem., Zermatt
94. Mahmoudian M, Michael A. 1992. Biocatalysts for production of chiral epoxides.Appl. Microbiol. Biotechnol. 37:23-27
95. Mahmoudian M, Michael A. 1992. Stereoselective epoxidation of phenyl allyl ether by alkene-utilizing bacteria. Appl. Microbiol. Biotechnol. 37:28-31
96. Mansuy D, Battioni P, Battioni JP. 1989. Chemical model systems for drug-metabolizing cytochrome P-450-dependent monooxygenases. Eur. J. Biochem. 184:267-85
97. May SW, Abbott BJ. 1973. Enzymatic epoxidation. II. Comparison between the epoxidation and hydroxylation reactions catalyzed by the ω-hydroxylation system of Pseudomonas oleovorans. J. Biol. Chem. 248:1725-30
98. May SW, Schwartz RD, Abbott BJ, Zaborsky OR. 1975. Structural effects on the reactivity of substrates and inhibitors in the epoxidation system of Pseudomonas oleovorans. Biochim. Biophys. Acta 403:245-55
99. May SW, Steltenkamp MS, Schwartz RD, McCoy CJ. 1976. Stereoselective formation of diepoxides by an enzyme system of Pseudomonas oleovorans. J. Am. Chem. Soc. 98:7856-58
100. McCarthy MB, White RE. 1983. Functional differences between peroxidase compound I and the cytochrome P-450 reactive oxygen intermediate. J. Biol. Chem. 258:9153-58
101. McMillan DC, Cerniglia CE, Fu PP. 1987. Stereoselective fungal metabolism of 7,12-dimethylbenz(α)anthracene - identification and enantiomeric resolution of a K-region dihydrodiol. Appl. Environ. Microbiol. 53:2560-66
102. Michaels BC, Fulco AJ, Ruettinger RT. 1980. Hydration of 9,10-epoxypalmitic acid by a soluble enzyme from Bacillus megaterium. Biochem. Biophys Res. Commun. 92:1189-95
103. Mischitz M, Faber K. 1994. Asymmetric opening of an epoxide by azide catalyzed by an immobilized enzyme preparation from Rhodococcus sp. Tetrahedron Lett. 35:81-84
104. Mischitz M, Faber K, Willetts A. 1995. Isolation of a highly enantioselective epoxide hydrolase from Rhodococcus sp. MAJ 11216. Tetrahedron Asymmetry 17:893-98
105. Mischitz M, Kroutil W, Wandel U, Faber K. 1995. Asymmetric microbial hydrolysis of epoxides. Tetrahedron Asymmetry 6:1261-72
106. Morisseau C, Nellaiah H, Archelas A, Furstoss R, Baratti JC. 1997. Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger. Enzyme Microb. Technol. 20:446-52
107. Morris DR, Hager LP. 1966. Chloroperoxidase. I. Isolation and properties of the crystalline glycoprotein. J. Biol. Chem. 241:1763-68
108. Morrison M, Schonbaum GR. 1976. Peroxidase-catalyzed halogenation. Anna. Rev. Biochem. 45:861-88
109. Murmann W, Rumore G, Gamba A. 1967. Pharmacological properties of 1-(4′-nitrophenyl)-2-isopropylamino-ethanol (INPEA). A new β-adrenergic receptor antagonist. Bull. Chim. Farm. 106:251-68
110. Nagasawa T, Nakamura T, Yu F, Watan abe I, Yamada H. 1992. Purification and characterization of halohydrin hydrogenhalide lyase from a recombinant Escherichia coli containing the gene from a Corynebacterium sp. Appl. Microbiol. Biotechnol. 36:478-82
111. Nakamura T, Nagasawa T, Yu F, Watanabe I, Yamada H. 1992. 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. 174:7613-19
112. Nakamura T, Nagasawa T, Yu F, Watanabe I, Yamada H. 1994. Purification and characterization of two epoxide hydrolases from Corynebacterium sp. strain N-1074. Appl. Environ. Microbiol. 60:4630-33
113. Nakamura T, Yu F, Mizunashi W, Watanabe I. 1991. Microbial transformation of prochiral 1,3-dichloro-2-propanol into optically active 3-chloro-1,2-propanediol. Agric. Biol. Chem. 55:1931-33
114. Neidleman SL. 1980. Use of enzymes as catalysts for alkene oxide production. Hydrocarb. Process, pp. 135-38
115. Neidleman SL, Levine SD. 1968. Enzymatic bromohydrin formation. Tetrahedron Lett. 37:4057-59
116. Nellaiah H, Morisseau C, Archelas A, Furstoss R, Baratti JC. 1996. Enantioselective hydrolysis of p-nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger. Biotechnol. Bioeng. 49:70-77
117. Niehaus WG, Schroepfer GJ. 1967. Enzymatic stereospecificity in the hydration of epoxy fatty acids. Stereospecific incorporation of the oxygen of water. J. Biol. Chem. 89:4227-28
118. Nöthe C, Hartmans S. 1994. Formation and degradation of styrene oxide stereoisomers by different microorganisms. Biocatalysis 10:219-25
119. Ohno M, Okura I. 1990. On the reaction mechanism of alkene epoxidation with Methylosinus trichosporium (OB3b). J. Mol. Catal. 61:113-22
120. Ohta H, Tetsukawa H. 1979. Asymmetric epoxidation of long chain terminal olefins by Corynebacterium equi IFO 3730. Agric. Biol. Chem. 43:2099-104
121. Onumonu AN, Colocoussi A, Matthews C, Woodland MP, Leak DJ. 1994. Microbial alkene epoxidation - merits and limitations. Biocatalysis 10:211-18
122. Ortiz de Montellano PR. 1987. Cytochromes P-450. New York: Plenum. 556 pp.
123. Ortiz de Montellano PR, Choe YS, Depillis G, Catalano CE. 1987. Structure-mechanism relationships in hemoproteins. Oxygenations catalyzed by chloroperoxidase and horseradish peroxidase. J. Biol. Chem. 262:11641-46
124. Ortiz de Montellano PR, Fruetel JA, Collins JR, Camper DL, Loew GH. 1991. Theoretical and experimental analysis of the absolute stereochemistry of cis-β-methylstyrene epoxidation by cytochrome P-450cam. J. Am. Chem. Soc. 113:3195-96
125. Osprian I, Kroutil W, Mischitz M, Faber K. 1997. Biocatalytic resolution of 2-methyl-2-(aryl)alkyloxiranes using novel bacterial epoxide hydrolases. Tetrahedron Asymmetry. 18:65-71
126. Otto PPJHL, Stein F, van der Willigen CA. 1988. A bio-organic synthesis of (+)-disparlure, sex pheromone of Lymantria dispar (gypsy moth). Agric. Ecosys. Environ. 21:121-23
127. Palmer JT. 1985. US Patent No. 4552695
128. Pedragosa-Moreau S, Archelas A, Fursloss R. 1993. Microbiological transformations. 28. Enantiocomplementary epoxide hydrolyses as a preparative access to both enantiomers of styrene oxide. J. Org. Chem. 58:5533-36
129. Pedragosa-Moreau S, Archelas A, Furstoss R. 1994. Microbiological transformations. 29. Enantioselective hydrolysis of epoxides using microorganisms: a mechanistic study. Bioorg. Med. Chem. 2:609-16
130. Pedragosa-Moreau S, Archelas A, Furstoss R. 1995. Epoxydes enantiopurs: obtention par voie chimique ou par voie enzymatique. Bull. Soc. Chim. Fr. 132:769-800
131. Pedragosa-Moreau S, Archelas A, Furstoss R. 1996. Microbial transformations. 31. Synthesis of enantiopure epoxides and vicinal diols using fungal epoxide hydrolase mediated hydrolysis. Tetrahedron Lett. 37:3319-22
132. Pedragosa-Moreau S, Archelas A, Furstoss R. 1996. Microbial transformations. 32. Use of epoxide hydrolase mediated biohydrolysis as a way to enantiopure epoxides and vicinal diols: application to substituted styrene oxide derivatives. Tetrahedron 52:4593-606
133. Pedragosa-Moreau S, Morisseau C, Zylber J, Archelas A, Baratti JC, Furstoss R. 1996. Microbiological transformations. 33. Fungal epoxide hydrolases applied to the synthesis of enantiopure para-substituted styrene oxides. A mechanistic approach. J. Org. Chem. 61:7402-7
134. Pfenninger A. 1986. Asymmetric epoxidation of allylic alcohols: the Sharpless epoxidation. Synthesis 2:89-116
135. Poulos TL, Raag R. 1992. Cytochrome P-450cam: crystallography, oxygen activation, and electron transfer. Faseb J. 6:674-79
136. Raag R, Poulos TL. 1991. Crystal structures of cytochrome P-450cam complexed with camphane, thiocamphor, and adamantane: factors controlling P-450 substrate hydroxylation. Biochemistry 30:2674-84
137. Ramakrishnan K, Oppenhuizen ME, Saunders S, Fisher J. 1983. Stereoselectivity of chloroperoxidase-dependent halogenation. Biochemistry 22:3271-77
138. Rigby SR, Matthews CS, Leak DJ. 1994. Epoxidation of styrene and substituted styrenes by whole cells of Mycobacterium sp. M156. Bioorg. Med. Chem. 2:553-56
139. Ruettinger RT, Fulco AJ. 1981. Epoxidation of unsaturated fatty acids by a soluble cytochrome P-450-dependent system from Bacillus megaterium. J. Biol. Chem. 256:5728-34
140. Ruettinger RT, Griffith GR, Coon MJ. 1977. Characterisation of the ω-hydroxylase of Pseudomonas oleovorans as a non heme iron protein. Arch. Biochem. Biophys. 183:528-37
141. Ryan DE, Levin W, Reik LM, Thomas PE. 1982. Enzyme. Xenobiotica 12:727-44
142. Sato H. 1975. Jpn. Patent No. 75140684
143. Schurig V, Betschinger F. 1992. Metal-mediated enantioselective access to unfonctionalized aliphatic oxiranes - prochiral and chiral recognition. Chem. Rev. 92:873-88
144. Seki Y, Shimoda M, Sugimori D, Okura I. 1994. Epoxidation of allyl compounds with Methylosinus trichosporium (OB3b): stereoselectivity of methane monooxygenase. J. Mol. Catal. 87L:17-19
145. Seu YB, Lim TK, Kim CJ, Kang SC. 1995. Preparation of enantiomerically pure (R)-2-butyryloxymethylglycidol by lipase-catalyzed asymmetric hydrolysis. Tetrahedron Asymmetry 6:3009-14
146. Sono M, Roach MP, Coulter ED, Dawson JH. 1996. Heme-containing oxygenases. Chem. Rev. 96:2841-87
147. Stinson SC. 1993. Chiral drugs. Wave of new enantiomer products set to flood market. Chem. Eng. News 27:38-63
148. Suzuki Y, Marumo S. 1972. Fungal metabolism of (+/-)-epoxyfarnesol and its absolute stereochemistry. Tetrahedron Lett. 19:1887-90
149. Takahashi O, Umezawa J, Furuhashi K, Takagi M. 1989. Stereocontrol of a tertiary hydroxyl group via microbial epoxidation. A facile synthesis of prostaglandine ω-chains. Tetrahedron Lett. 30:1583-84
150. Tseng HF, Laughlin LT, Lin S, Armstrong RN. 1996. The catalytic mechanism of microsomal epoxide hydrolases involve reversible formation and rate-limiting hydrolysis of the alkyl-enzyme intermediate. J. Am. Chem. Soc. 118:9436-37
151. Ueda T, Coon JM. 1972. Enzymatic ω oxidation. VII. Reduced diphosphopyridine nucleotide-rubredoxin reductase: properties and function as an electron carrier in ω hydroxylation. J. Biol. Chem. 247:5010-16
152. Van Ginkel CG, Welten HGJ, de Born JAM. 1986. Epoxidation of alkenes by alkene-grown Xanthobacter sp. Appl. Micmbiol. Biotechnol. 24:334-37
153. Van Pee KH. 1995. B.C.G. halogenation. In Enzyme Catalysis in Organic Synthesis. A Comprehensive Handbook, ed. K Drauz, H Waldmann, 2:783-807. Weinheim: VCH
154. Vilter H. 1983. Peroxidases from phaeophyceae. 4. Fractionation and location of peroxidase isoenzymes in Ascophyllum nodosum. Bot. Mar. 26:451-55
155. Wackett LP, Gibson DT. 1982. Metabolism of xenobiotic compounds by enzymes in cell-extracts of the fungus Cunninghamella elegans. Biochem. J. 205:117-22
156. Wallar BJ, Lipscomb JD. 1996. Dioxygen activation by enzymes containing binuclear non-heme iron clusters. Chem. Rev. 96:2625-57
157. Wandel U, Mischitz M, Kroutil W, Faber K. 1995. Highly selective asymmetric hydrolysis of 2,2-disubstituted epoxides using lyophilized cells of Rhodococcus sp. ncimb 11216. J. Chem. Soc. Perkin Trans. 1:735-36
158. Weijers CAGM, de Haan A, de Bont JAM. 1988. Chiral resolution of 2,3-epoxyalkanes by Xanthobacter Py2. Appl. Microbiol. Biotechnol. 27:337-40
159. Weijers CAGM, de Haan A, de Bont JAM. 1988. Microbial production and metabolism of epoxides. Microbiol. Sci. 5:156-59
160. Weijers CAGM, Litjens MJJ, de Boni JAM. 1992. Synthesis of optically pure 1,2-epoxypropane by microbial asymmetric reduction of chloroacetone. Appl. Microbiol. Biotechnol. 38:297-300
161. Weijers CAGM, Van Ginkel CG, de Bont JAM. 1988. Enantiomeric composition of lower epoxyalkanes produced by methane-, alkane-, and alkene-utilizing bacteria. Enzyme Microb. Technol. 10:214-18
162. White RF. 1980. US Paient No. 2054310
163. White RF, Birnbaum J, Meyer RT, Broeke JT, Chemerda JM, Demain AL. 1971. Microbial epoxidation of cis-propenylphosphonic to (-)-cis-1,2-epoxypropylphosphonic acid. Appl. Microbiol 22:55-60
164. Wiesner W, Van Pee KH, Lingens F. 1988. Purification and characterisation of a novel bacterial non-heme chloroperoxidase from Pseudomonas pyrrocinia. J. Biol. Chem. 263:13725-32
165. Wixtrom RN, Hammock BD. 1985. Membrane-bound and soluble fraction epoxide hydrolases: methodological aspects. In Biochemical Pharmacology and Toxicology, ed. D Zakim, DA Vessey, 1:1-93. New York: Wiley
166. Woods NR, Murrell JC. 1991. Epoxidation of gaseous alkenes by a Rhodococcus sp. Biotechnol. Lett. 12:409-14
167. Wu DR, Cramer SM, Beifort G. 1993. Kinetic resolution of racemic glycidyl butyrate using a multiphase membrane enzyme reactor. Experiments and model verification. Biotechnol. Bioeng. 41:979-90
168. Wubbolts MG, Hoven J, Melgert B, Witholt B. 1994. Efficient production of optically active styrene epoxides in two-liquid phase cultures. Enzyme Microb. Technol. 16:887-94
169. Wubbolts MG, Noordman R, Van Beilen JB, Witholt B. 1995. Enantioselective oxidation by non-heme iron monooxygenases from Pseudomonas. Recueil des Travaux Chimiques des Pays-Bas 114:139-44
170. Wubbolts MG, Panke S, Beilen JB, Witholt B. 1996. Enantioselective oxidation by non-heme iron monooxygenases from Pseudomonas. Chimia 50:436-37
171. Wynberg H, ten Hoeve W. 1989. Eur. Patent Appl. 0342903AI
172. Zaks A, Dodds DR. 1995. Chloroperoxidase-catalyzed asymmetric oxidations: substrate specificity and mechanistic study. J. Am. Chem. Soc. 117:10419-24
173. Zeldin DC, Dubois RN, Falck JR, Capdevila JH. 1995. Molecular cloning, expression and characterization of an endogenous human cytochrome P-450 arachidonic acid epoxygenase isoform. Arch. Biochem. Biophys. 322:76-86
174. Zhang J, Reddy J, Roberge C, Senanayake C, Greasham R, Chartrain M. 1995. Chiral bio-resolution of racemic indene oxide by fungal epoxide hydrolases. J. Ferment. Bioeng. 80:244-46
175. Zhang XM, Archelas A, Furstoss R. 1991. Microbiological transformations. 19. Asymmetric dihydroxylation of the remote double bond of geraniol: a unique stereochemical control allowing easy access to both enantiomers of geraniol-6,7-diol. J. Org. Chem. 56:3814-17