Baeyer-Villiger Oxidations

Enzyme Catalysis in Organic Synthesis, Third Edition

Volumn 3, Issue , 2012, Pages 1439-1485

  Mihovilovic, Marko D ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Baeyer Villiger monooxygenase; Baeyer Villiger oxidation; Biocatalysis; Cofactor recycling; Enzyme engineering; Synthetic applications

Indexed keywords

EID: 84872189083     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527639861.ch33     Document Type: Chapter

References (242)

1. Baeyer, A. and Villiger, V. (1899) Chem. Ber., 32, 3625-3633.
2. Krow, G.R. (1993) Org. React., 43, 251-798.
3. Renz, M. and Meunier, B. (1999) Eur. J. Org. Chem., 737-750.
4. Mihovilovic, M.D., Rudroff, F., and Grötzl, B. (2004) Curr. Org. Chem., 8, 1057-1069.
5. Turfitt,G.E.(1948)Biochem.J.,42,376-383.
6. Fried, J., Thoma, R.W., and Klingsberg, A. (1953) J. Am. Chem. Soc., 75, 5764-5765.
7. Peterson, D.H., Eppstein, S.H., Meister, P.D., Murray, H.C., Leigh, H.M., Weintraub, A., and Reinecke, L.M. (1953) J. Am. Chem. Soc., 75, 5768-5769.
8. Townsend, C.A., Christensen, S.B., and Davis, S.G. (1982) J. Am. Chem. Soc., 104, 6154-6155.
9. Wright, J.L.C., Hu, T., McLachlan, J.L., Needham, J., and Walter, J.A. (1996) J. Am. Chem. Soc., 118, 8757-8758.
10. Damtoft, S., Franzyk, H., and Jensen, S.R. (1995) Phytochemistry, 40, 773-784.
11. Prairie, R.L. and Talalay, P. (1963) Biochemistry, 2, 203-208.
12. Forney, F.W. and Markovetz, A.J. (1969) Biochem. Biophys. Res. Commun., 37, 31-38.
13. Conrad, H.E.,DuBus, R., Namtvedt, M.J., and Gunsalus, I.C. (1965) J. Biol. Chem., 240, 495-503.
14. Willetts, A. (1997) Trends Biotechnol., 15, 55-62.
15. van Berkel, W.J.H., Kamerbeek, N.M., and Fraaije, M.W. (2006) J. Biotechnol., 124, 670-689.
16. Fraaije, M.W., Kamerbeek, N.M., van Berkel, W.J.H., and Janssen, D.B. (2002) FEBS Lett., 518, 43-47.
17. Van Beilen, J.B., Mourlane, F., Seeger, M.A., Kovac, J., Li, Z., Smits, T.H.M., Fritsche, U., and Witholt, B. (2003) Environ. Microbiol., 5, 174-182.
18. Stewart, J.D., Reed, K.W., and Kayser, M.M. (1996) J. Chem. Soc., Perkin Trans. 1, 755-757.
19. Kayser, M.M. (2009) Tetrahedron, 65, 947-974
20. Mihovilovic, M.D. (2006) Curr. Opin. Chem., 10, 1265-1287
21. Kamerbeek, N.M., Janssen, D.B., van Berkel, J.H., and Fraaije, M.W. (2003) Adv. Synth. Catal., 345, 667-678
22. Mihovilovic, M.D., Muller, B. and Stanetty, P. (2002) Eur. J. Org. Chem., 3711-3730.
23. Alphand, V.A., Fraaije, M.W., Mihovilovic, M.D., and Ottolina, G. (2009) SecondGeneration Baeyer-Villiger Biocatalysts in Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions (eds W.D. Fessner and T. Anthonsen), Wiley-VCH Verlag GmbH, Weinheim, pp. 339-368;
24. Fraaije, M.W. and Janssen, D.B. (2007) Biocatalytic Scope of Baeyer-Villiger Monooxygenases in Modern Biooxidation. Enzymes, Reactions and Applications (eds R.D. Schmid and V.B. Urlacher), Wiley-VCH Verlag GmbH, Weinheim, pp. 77-97.
25. Donoghue, N.A. and Trudgill, P.W. (1975) Eur. J. Biochem., 60, 1-7.
26. Iwaki, H., Hasegawa, Y., Teraoka, M., Tokuyama, T., Bergeron, H., and Lau, P.C.K. (1999) Appl. Environ. Microbiol., 65, 5158-5162.
27. Cheng, Q., Thomas, S.M., Kostichka, K., Valentine, J.R., and Nagarajan, V. (2000) J. Bacteriol., 182, 4744-4751.
28. Brzostowicz, P., Walters, D.M., Thomas, S.M., Nagarajan, V., and Rouviere, P.E. (2003) Appl. Environ. Microbiol., 69, 334-342.
29. Brzostowicz, P.C., Gibson, K.L., Thomas, S.M., Blasko, M.S., and Rouviere, P.E. (2000) J. Bacteriol., 182, 4241-4248.
30. Wright, J.L.C., Hu, T., MacLachlan, J.L., Needham, J., and Walter, J.A. (1996) J. Am. Chem. Soc., 118, 8758-8759.
31. Cheng, Q., Thomas, S.M., and Rouviere, P. (2002) Appl. Microbiol. Biotechnol., 58, 238-242.
32. Ryerson, C.C., Ballou, D.P., and Walsh, C. (1982) Biochemistry, 21, 2644-2655.
33. Sheng, D., Ballou, D.P., and Massey, V. (2001) Biochemistry, 40, 11156-11167.
34. Torres-Pazmino, D.E., Baas, B.-J., Janssen, D.B., and Fraaije, M.W. (2008) Biochemistry, 47, 4082-4093.
35. Criegee, R. (1948) Liebigs Ann. Chem., 560, 127-141.
36. Malito, E., Alfieri, A., Fraaije, M.W., and Mattevi, A. (2004) Proc. Nat. Acad. Sci. USA, 101, 13157-13162.
37. Fraaije, M.W., Kamerbeek, N.M., Heidekamp, A.J., Fortin, R., and Janssen, D.B. (2004) J. Biol. Chem., 279, 3354-3360.
38. Mirza, I.A.M., Yachnin, B.J., Wang, S., Grosse, S., Bergeron, H., Imura, A., Iwaki, H., Hasegawa, Y., Lau, P.C.K., and Berghuis, A.M. (2009) J. Am. Chem. Soc., 131, 8848-8855.
39. de Gonzalo, G., Ottolina, G., Fraaije, M.W., and Carrea, G. (2005) Chem. Commun., 3724-3726.
40. Alphand, V., Carrea, G.,Wohlgemuth, R., Furstoss, R., and Woodley, J.M. (2003) Trends Biotechnol., 21, 318-323.
41. Doig, S.D., O'Sullivan, L.M., Patel, S., Ward, J.M., and Woodley, J.M. (2001) Enzyme Microb. Technol., 28, 265-274.
42. Cheesman, M.J., Kneller, B., Kelly, E.J., Thompson, S.J., Yeung, C.K., Eaton, D.L., and Rettie, A.E. (2001) Protein Expression Purif., 21, 81-86.
43. Schwarz-Linek, U., Krödel, A., Ludwig, F.-A., Schulze, A., Rissom, S., Kragl, U., Tishkov, V.I., and Vogel, M. (2001) Synthesis, 947-951.
44. de Gonzalo, G., Ottolina, G., Zambianchi, F., Fraaije, M.W., and Carrea, G. (2006) J. Mol. Catal. B.: Enzym., 39, 91-97.
45. Willetts, A.J., Knowles, C.J., Levitt, M.S., Roberts, S.M., Sandey, H., and Shipston, N.F. (1991) J. Chem. Soc., Perkin Trans. 1, 1608-1610.
46. Grogan, G., Roberts, S. and Willetts, A.J. (1992) Biotechnol. Lett., 14, 1125-1130.
47. Secundo, F., Carrea, G., Riva, S., Battistel, E., and Bianchi, D. (1993) Biotechnol. Lett., 15, 865-870.
48. Hogan, M.C. and Woodley, J.M. (2000) Chem. Eng. Sci., 55, 2001-2008.
49. Zambianchi, F., Pasta, P., Carrea, G., Colonna, S., Gaggero, N., and Woodley, J.M. (2002) Biotechnol. Bioeng., 78, 489-496.
50. Willetts, A.J., Knowles, C.J., Levitt, M.S., Roberts, S.M., Sandey, H., and Shipston, N.F. (1991) J. Chem. Soc., Perkin Trans. 1, 1608-1610.
51. Grogan, G., Roberts, S., and Willetts, A.J. (1992) Biotechnol. Lett., 14, 1125-1130.
52. Zambianchi, F., Pasta, P., Carrea, G., Colonna, S., Gaggero, N., and Woodley, J.M. (2002) Biotechnol. Bioeng., 78, 489-496.
53. Atia, K.S. (2005) Radiat. Phys. Chem., 73, 91-99.
54. Narita, J., Okano, K., Tateno, T., Tanino, T., Sewaki, T., Sung, M.-H., Fukuda, H., and Kondo, A. (2006) Appl. Microbiol. Biotechnol., 70, 564-572.
55. Liu, D., Schmid, R.D., and Rusnak, M. (2006) Appl. Microbiol. Biotechnol., 72, 1024-1032.
56. Metcalf, W.W. and Wolfe, R.S. (1998) J. Bacteriol., 180, 5547-5558.
57. Costas, A.M., White, A.K., and Metcalf, W.W. (2001) J. Biol. Chem., 276, 17429-17436.
58. Vrtis, J.M., White, A.K., Metcalf, W.W., and van der Donk, W.A. (2002) Angew. Chem., 114, 3391-3393.
59. Vrtis, J.M., White, A.K., Metcalf, W.W., and van der Donk, W.A. (2002) Angew. Chem. Int. Ed., 41, 3257-3259.
60. Woodyer, R.D., van der Donk, W.A., and Zhao, H. (2003) Biochemistry, 42, 11604-11614.
61. Torres Pazmino, D.E., Snajdrova, R., Baas, B.-J., Ghobrial, M., Mihovilovic, M.D., and Fraaije, M.W. (2008) Angew. Chem. Int. Ed., 47, 2275-2278.
62. Pazmino, D.E.T., Riebel, A., de Lange, J., Rudroff, F., Mihovilovic, M.D., and Fraaije, M.W. (2009) ChemBioChem, 10, 2595-2598.
63. Hollmann, F., Hofstetter, K., and Schmid, A. (2006) Trends Biotechnol., 24, 163-171.
64. de Gonzalo, G., Ottolina, G., Carrea, G., and Fraaije, M.W. (2005) Chem. Commun., 3724-3726.
65. Hollmann, F., Taglieber, A., Schulz, F., and Reetz, M.T. (2007) Angew. Chem. Int. Ed., 46, 2903-2906.
66. Taglieber, A., Schulz, F., Hollmann, F., Rusek, M., and Reetz, M.T. (2008) ChemBioChem, 9, 565-572.
67. Rioz-Martinez, A., de Gonzalo, G., Torres-Pazmino, D.E., Fraaije, M.W., and Gotor, V. (2009) Eur. J. Org. Chem., 2526-2532.
68. Rodrigez, C., de Gonzalo, G., Torres-Pazmino, D.E., Fraaije, M.W., and Gotor, V. (2008) Tetrahedron: Asymmetry, 19, 197-203.
69. Mihovilovic, M.D., Snajdrova, R., Winninger, A., and Rudroff, F. (2005) Synlett, 2751-2754.
70. Doig, S.D., Simpson, H., Alphand, V., Furstoss, R., and Woodley, J.M. (2003) Enzyme Microbiol. Technol., 32, 347-355.
71. Rudroff, F., Alphand,V., Furstoss, R., and Mihovilovic, M.D. (2006) Org. Process Res. Develop., 10, 599-604.
72. Walton, A.Z. and Stewart, J.D. (2002) Biotechnol. Prog., 18, 262-268.
73. Walton, A.Z. and Stewart, J.D. (2004) Biotechnol. Prog., 20, 403-411.
74. Simpson, H., Alphand, V., and Furstoss, R. (2001) J. Mol. Catal. B: Enz., 16, 101-108.
75. Law, H.E.M., Baldwin, C.V.F., Chen, B.H., and Woodley, J.M. (2006) Chem. Eng. Sci., 61, 6646-6652.
76. Clouthier, C.M. and Kayser, M.M. (2007) J. Mol. Catal. B.: Enzym., 46, 32-36.
77. Hilker, I., Baldwin, C., Alphand, V., Furstoss, R., Woodley, J., and Wohlgemuth, R. (2006) Biotechnol. Bioeng., 93, 1138-1144.
78. Baldwin, C.V.F. and Woodley, J.M. (2006) Biotechnol. Bioeng., 95, 362-369.
79. Hilker, I., Wohlgemuth, R., Alphand, V., and Furstoss, R. (2005) Biotechnol. Bioeng., 92, 702-710.
80. Doig, S.D., Avenell, P.J., Bird, P.A., Gallati, P., Lander, K.S., Lye, G.J., Wohlgemuth, R., and Woodley, J.M. (2002) Biotechnol. Prog., 18, 1039-1046.
81. Baldwin, C.V.F.,Wohlgemuth, R., and Woodley, J.M. (2008) Org. Proc. Res. Develop., 12, 660-665.
82. Yang, J.,Wang, S., Lorrain, M.-J., Rho, D., Abokitse, K., and Lau, P.C.K. (2009) Appl. Microbiol. Biotechnol., 84, 867-876.
83. Hilker, I., Gutierrez, M.C., Furstoss, R., Ward, J., Wohlgemuth, R., and Alphand, V. (2008) Nat. Protoc., 3, 546-554.
84. Hilker, I., Alphand, V., Wohlgemuth, R., and Furstoss, R. (2004) Adv. Synth. Catal., 346, 203-214.
85. Hilker, I., Gutierrez, M.C., Alphand, V., Wohlgemuth, R., and Furstoss, R. (2004) Org. Lett., 6, 1955-1958.
86. Wohlgemuth, R. (2006) Eng. Life Sci., 6, 577-583.
87. Stewart, J.D. (1998) Curr. Org. Chem., 2, 195-216.
88. Gibson, M., Nur-e-alam, M., Lipata, F., Oliveira, M.A., and Rohr, J. (2005) J. Am. Chem. Soc., 127, 17594-17595.
89. Beam, M.P., Bosserman, M.A., Noinaj, N., Whenkel, M., and Rohr, J. (2009) Biochemistry, 48, 4476-4487.
90. Jiang, J., Tetzlaff, C.N., Takamatsu, S., Iwatsuki, M., Komatsu, M., Ikeda, H., and Cane, D.E. (2009) Biochemistry, 48, 6431-6440.
91. Itagaki, E. (1986) J. Biochem., 99, 815-824.
92. Lebreton, J., Alphand, V., and Furstoss, R. (1996) Tetrahedron Lett., 37, 1011-1014.
93. Lebreton, J., Alphand, V., and Furstoss, R. (1997) Tetrahedron, 53, 145-160.
94. Quazzani-Chahdi, J., Buisson, D., and Azerad, R. (1987) Tetrahedron Lett., 28, 1109-1112.
95. Conrad, H.E., DuBus, R., Namtvedt, M.J., and Gunsalus, I.C. (1965) J. Biol. Chem., 240, 495-503.
96. Taylor, D.G., and Trudgill, P.W. (1986) J. Bacteriol., 165, 489-497.
97. Ougham, H.J., Taylor, D.G., and Trudgill, P.W. (1983) J. Bacteriol., 153, 140-152.
98. Bonsor, D., Butz, S.F., Solomons, J., Grant, S., Fairlamb, I.J.S., Fogg, M.J., and Grogan, G. (2006) Org. Biomol. Chem., 4, 1252-1260.
99. Snajdrova, R., Grogan, G., and Mihovilovic, M.D. (2006) Bioorg. Med. Chem. Lett., 16, 4813-4817.
100. Rehdorf, J., Kirschner, A., and Bornscheuer, U.T. (2007) Biotechnol. Lett., 29, 1393-1398.
101. Völker, A., Kirschner, A., Bornscheuer, U.T., and Altenbuchner, J. (2008) Appl. Microbiol. Biotechnol., 77, 1251-1260.
102. Kostichka, K., Thomas, S.M., Gibson, K.J., Nagarajan, V., and Cheng, Q. (2001) J. Bacteriol., 183, 6478-6486.
103. Kyte, B.G., Rouviere, P., Cheng, Q., and Stewart, J.D. (2004) J. Org. Chem., 69, 12-17.
104. Donoghue, N.A., Norris, D.B., and Trudgill, P.W. (1976) Eur. J. Biochem., 63, 175-192.
105. Chen, Y.-C.J., Peoples, O.P., and Walsh, C.T. (1988) J. Bacteriol., 170, 781-789.
106. Brzostowicz, P., Walters, D.M., Thomas, S.M., Nagarajan, V., and Rouviere, P.E. (2003) Appl. Environ. Microbiol., 69, 334-342.
107. Cheng, Q., Thomas, S.M., Kostichka, K., Valentine, J.R., and Nagarajan, V. (2000) J. Bacteriol., 182, 4744-4751.
108. Mihovilovic, M.D., Rudroff, F.,Grötzl, B., Kapitan, P., Snajdrova, R., Rydz, J., and Mach, R. (2005) Angew. Chem. Int. Ed., 44, 3609-3613.
109. Bramucci, M.G., Brzostowicz, P.C., Kostichka, K.N., Nagarajan, V., Rouviere, P.E., and Thomas, S.M. (2003) PCT Int. Appl. WO 2003020890.(2003) Chem. Abstr., 138, 233997.
110. Brzostowicz, P.C., Gibson, K.L., Thomas, S.M., Blasko, M.S., and Rouviere, P.E. (2000) J. Bacteriol., 182, 4241-4248.
111. Mihovilovic, M.D., Rudroff, F., Muller, B., and Stanetty, P. (2003) Bioorg. Med. Chem. Lett., 13, 1479-1482.
112. van Beilen, J.B., Mourlane, F., Seeger, M.A., Kovac, J., Li, Z., Smits, T.H.M., Fritsche, U., and Witholt, B. (2003) Environ. Microbiol., 5, 174-182.
113. Rial, D.V., Cernuchova, P., van Beilen, J.B., and Mihovilovic, M.D. (2008) J. Mol. Catal. B: Enzym., 50, 61-68.
114. Rial, D.V., Bianchi, D.A., Kapitanova, P., Lengar, A., van Beilen, J.B., and Mihovilovic, M.D. (2008) Eur. J. Org. Chem., 1203-1213.
115. Iwaki, H., Wang, S., Grosse, S., Bergeron, H., Nagahashi, A., Lertvorachon, J., Yang, J., Konishi, Y., Hasegawa, Y., and Lau, P.C.K. (2006) Appl. Environ. Microbiol., 72, 2707-2720.
116. Griffin, M. and Trudgill, P.W. (1976) Eur. J. Biochem., 63, 199-209.
117. Iwaki, H., Hasegawa, Y., Lau, P.C.K., Wang, S., and Kayser, M.M. (2002) Appl. Environ. Microbiol., 68, 5681-5684.
118. Kamerbeek, N.M., Moonen, M.J.H., van der Ven, J.G.M., van Berkel, W.J.H., Fraaije, M.W., and Janssen, D.B. (2001) Eur. J. Biochem., 268, 2547-2557.
119. Kamerbeek, N.M., Olsthorn, A.J.J., Fraaije, M.W., and Janssen, D.B. (2003) Appl. Environ. Microbiol., 69, 419-426.
120. Mihovilovic, M.D., Kapitan, P., Rydz, J., Rudroff, F., Ogink, F.H., and Fraaije, M.W. (2005) J. Mol. Catal. B: Enzym., 32, 135-140.
121. Rehdorf, J., Zimmer, C.L., and Bornscheuer, U.T. (2009) Appl. Environ. Microbiol., 75, 3106-3114.
122. Kirschner, A. and Bornscheuer, U.T. (2006) Angew. Chem. Int. Ed., 45, 7004-7006.
123. Kirschner, A., Altenbucher, J., and Bornscheuer, U.T. (2007) Appl. Microbiol. Biotechnol., 73, 1065-1072.
124. Szolkowy, C., Eltis, L.D., Bruce, N.C., and Grogan, G. (2009) ChemBioChem, 10, 1208-1217.
125. Malito, E., Alfieri, A., Fraaije, M.W., and Mattevi, A. (2004) Proc. Natl. Acad. Sci. USA, 101, 13157-13162.
126. Fraaije, M.W., Wu, J., Neuts, D.P.H.M., van Hellemond, E.W., Spelberg, J.H.L., and Janssen, D.B. (2005) Appl. Microbiol. Biotechnol., 66, 393-400.
127. Fraaije, M.W., Kamerbeek, N.M., Heidekamp, A.J., Fortin, R., and Janssen, D.B. (2004) J. Biol. Chem., 279, 3354-3360.
128. Morii, S., Sawamoto, S., Yamauchi, Y., Miyamoto, M., Iwami, M., and Itagaki, E. (1999) J. Biochem., 126, 624-631.
129. Mihovilovic, M.D., Rudroff, F.,Muller, B., and Stanetty, P. (2003) Bioorg.Med. Chem. Lett., 13, 1479-1482.
130. Mihovilovic, M.D., Kapitan, P. and Kapitanova, P. (2008) ChemSusChem, 1, 143-148.
131. Mihovilovic, M.D. and Kapitan, P. (2004) Tetrahedron Lett., 45, 2751-2754.
132. Beneventi, E., Ottolina, G., Carrea, G., Panzeri, W., Fronza, G., and Lau, P.C.K. (2009) J. Mol. Catal. B: Enzym., 58, 164-168.
133. Bruice, T.C. (1980) Acc. Chem. Res., 13, 256-262.
134. Ghisla, S. and Massey, V. (1989) Eur. J. Biochem., 181, 1-17.
135. Colonna, S., Gaggero, N., Richelmi, C., and Pasta, P. (2000) NATO Sci. Ser. 1, 33, 133-160.
136. Light, D.R., Waxman, D.J. and Walsh, C. (1982) Biochemistry, 21, 2490-2498.
137. Secundo, F., Carrea, G., Dallavalle, S., and Franzosi, G. (1993) Tetrahedron: Asymmetry, 4, 1981-1982.
138. Beecher, J., Richardson, P., and Willetts, A. (1994) Biotechnol. Lett., 16, 909-912.
139. Pasta, P., Carrea, G., Holland, H.L., and Dallavalle, S. (1995) Tetrahedron: Asymmetry, 6, 933-936.
140. Kelly, D.R., Knowles, J.C., Mahdi, J.G., Taylor, I.N., and Wright, M.A. (1996) Tetrahedron: Asymmetry, 7, 365-368.
141. Colonna, S., Gaggero, N., Pasta, P., and Ottolina, G. (1996) Chem. Commun., 2303-2307.
142. Colonna, S., Gaggero, N., Carrea, G., and Pasta, P. (1997) Chem. Commun., 439-440.
143. Holland, H.L., Gu, J.-X., Kerridge, A., and Willetts, A. (1999) Biocatal. Biotransform., 17 305-317.
144. Colonna, S., Gaggero, N., Bertinotti, A., Carrea, G., Pasta, P., and Bernardi, A. (1995) J. Chem. Soc., Chem. Commun., 1123-1124.
145. Alphand, V., Gaggero, N., Colonna, S., and Furstoss, R. (1996) Tetrahedron Lett., 37, 6117-6120.
146. Alphand, V., Gaggero, N., Colonna, S., Pasta, P., and Furstoss, R. (1997) Tetrahedron, 53, 9695-9706.
147. Colonna, S., Gaggero, N., Carrea, G., and Pasta, P. (1998) Chem. Commun., 415-416.
148. de Gonzalo, G., Ottolina, G.,Zambianchi, F., Fraaije, M.W., and Carrea, G. (2006) J. Mol. Catal. B: Enzym., 39, 91-97.
149. Ottolina, G., Bianchi, S., Belloni, B., Carrea, G., and Danieli, B. (1999) Tetrahedron Lett., 40, 8483-8486.
150. Latham, J.A. Jr. and Walsh, C. (1986) J. Chem. Soc., Chem. Commun., 527-528.
151. Latham, J.A. Jr., Branchaud, B.P. Jr., Chen, Y.-C.J., and Walsh, C. (1986) J. Chem. Soc., Chem. Commun., 528-530.
152. Latham, J.A. and Walsh, C. (1987) J. Am. Chem. Soc., 109, 3421-3427.
153. Mihovilovic, M.D., Müller, B., Kayser, M.M., Stewart, J.D., Fröhlich, J., Stanetty, P., and Spreitzer, H. (2001) J. Mol. Catal. B: Enzym., 11, 349-353.
154. Mihovilovic, M.D., Grötzl, B., Kandioller, W., Muskotal, A., Snajdrova, R., Rudroff, F., and Spreitzer, H. (2008) Chem. Biodivers., 5, 490-498.
155. Colonna, S., Gaggero, N., Carrea, G., Ottolina, G., Pasta, P., and Zambianchi, F. (2002) Tetrahedron Lett., 43, 1797-1799.
156. Garcia-Urdiales, E., Alfonso, I., and Gotor,V. (2005) Chem. Rev., 105, 313-354.
157. Rudroff, F., Rydz, J., Ogink, F., Fink, M., and Mihovilovic, M.D. (2007) Adv. Synth. Catal., 349, 1436-1444.
158. Taschner, M.J., Black, D.J., and Chen, Q.-Z. (1993) Tetrahedron: Asymmetry, 4, 1387-1390.
159. Mihovilovic, M.D., Rudroff, F.,Grötzl, B., and Stanetty, P. (2005) Eur. J. Org. Chem., 1479-1482.
160. Stewart, J.D., Reed, K.W.,Martinez, C.A., Zhu, J., Chen, G., and Kayser, M.M. (1998) J. Am. Chem. Soc., 120, 3541-3548.
161. Iwaki, H., Hasegawa, Y., Wang, S., Kayser, M.M., and Lau, P.C. (2002) Appl. Environ. Microbiol., 68, 5671-5684.
162. Mihovilovic, M.D., Chen, G., Wang, S., Kyte, B., Rochon, F., Kayser, M.M., and Stewart, J.D. (2001) J. Org. Chem., 66, 733-738.
163. Wang, S., Kayser, M.M., Iwaki, H., and Lau, P.C.K. (2003) J. Mol. Catal. B: Enzym., 22, 211-218.
164. Taschner, M.J. and Peddada, L. (1992) J. Chem. Soc., Chem. Commun., 1384-1385.
165. Mihovilovic, M.D., Muller, B., Schulze, A., Stanetty, P., and Kayser, M.M. (2003) Eur. J. Org. Chem., 2243-2249.
166. Snajdrova, R., Braun, I., Bach, T., Mereiter, K., and Mihovilovic, M.D. (2007) J. Org. Chem., 72, 9597-9603.
167. Chen, C.-S., Fujimoto, Y., Girdaukas, G., and Sih, C.J. (1982) J. Am. Chem. Soc., 104, 7294-7299.
168. Martin, V.S., Woodard, S.S., Katsuki, T., Yamada, Y., Ikeda, M., and Sharpless, K.B. (1981) J. Am. Chem. Soc., 103, 6237-6240.
169. Gredig, G. and Fajans, K. (1908) Chem. Ber., 41, 752-763.
170. Bes, M.T., Villa, R., Roberts, S.M., Wan, P.W.H., and Willetts, A.J. (1996) J. Mol. Catal. B: Enzym., 1, 127-134.
171. Kayser, M.M., Chen, G., and Stewart, J. (1998) J. Org. Chem., 63, 7103-7106.
172. Berezina, N., Alphand, V., and Furstoss, R. (2002) Tetrahedron: Asymmetry, 13, 1953-1955.
173. Alphand, V., Furstoss, R., Pedragosa-Moreau, S., Roberts, S.M., and Willetts, A.J. (1996) J. Chem. Soc., Perkin Trans. 1, 1867-1872.
174. Stewart, J.D., Kieth, W.R., Zhu, J., Chen, G., and Kayser, M.M. (1996) J. Org. Chem., 61, 7652-7653.
175. Schwarz-Linek, U., Krödel, A., Ludwig, F.-A., Schulze, A., Rissom, S., Kragl, U., Tishkov, V.I., and Vogel, M. (2001) Synthesis, 947-951.
176. Adger, B., Bes, M.T., Grogan, G., McCague, R., Podragosa-Moreau, S., Roberts, S.M., Villa, R.,Wan, P.W.H., and Willetts, A.J. (1997) Bioorg.Med. Chem., 5, 253-261.
177. Cripps, R.E. (1975) Biochem. J., 152, 233-241.
178. Cripps, R.E., Trudgill, P.W., and Whateley, J.G. (1978) Eur. J. Biochem, 175-186.
179. Higson, F.K. and Focht, D.D. (1990) Appl. Environ. Microbiol, 56, 3678-3685.
180. Forney, F.W., Markovetz, A.J., and Kallio, R.E. (1967) J. Bacteriol., 93, 649-655.
181. Britton, L.N., Brand, J.M., and Markovetz, A.J. (1974) Biochim. Biophys. Acta, 369, 45-49.
182. Hartmans, S. and DeBont, J.A.M. (1986) FEMS Microbiol. Lett., 36, 155-158.
183. Geitner, K., Kirschner, A., Rehdorf, J., Schmidt, M., Mihovilovic, M.D., and Bornscheuer, U.T. (2007) Tetrahedron: Asymmetry, 18, 892-895.
184. Rodriguez, C., de Gonzalo, G., Fraaije, M.W., and Gotor, V. (2007) Tetrahedron: Asymmetry, 18, 1338-1344.
185. Rodriguez, C., de Gonzalo, G., Torres Pazmino, D.E., Fraaije, M.W., and Gotor, V. (2008) Tetrahedron: Asymmetry, 19, 197-203.
186. Rehdorf, J., Lengar, A., Bornscheuer, U.T., and Mihovilovic, M.D. (2009) Bioorg. Med. Chem. Lett., 19, 3739-3743.
187. Berezina, N., Alphand, V., and Furstoss, R. (2002) Tetrahedron: Asymmetry, 13, 1953-1955.
188. Gutierrez, M.C., Furstoss, R., and Alphand,V. (2005) Adv. Synth. Catal., 347, 1051-1059.
189. Noyori, R., Sato, T., and Kobayashi, H. (1983)Bull.Chem.Soc.Jpn.,56,2661-2679.
190. Schwab, J.M. (1981) J. Am. Chem. Soc., 103, 1876-1878.
191. Schwab, J.M., Li, W.-B. and Thomas, L.P. (1983) J. Am. Chem. Soc., 105, 4800-4808.
192. Rioz-Martinez, A., de Gonzalo, G., Torres Pazmino, D.E., Fraaije, M.W., and Gotor, V. (2009) Eur. J. Org. Chem., 2526-2532.
193. Ludwig, T., Ermert, J., and Coenen, H.H. (2002) Nucl.Med. Biol., 29, 255-262.
194. Moonen, M.J.H., Westphal, A.H., Rietjens, I.M.C.M., and van Berkel, W.J.H. (2005) Adv. Synth. Catal., 347, 1027-1034.
195. Berezina, H., Kozma, E., Furstoss, R., and Alphand,V. (2007) Adv. Synth. Catal., 349, 2049-2053.
196. Cernuchova, P. and Mihovilovic, M.D. (2007) Org. Biomol. Chem., 5, 1715-1719.
197. Alphand,V. and Furstoss, R. (1992) J. Org. Chem., 57, 1306-1309.
198. Kelly, D.R., Knowles, C.J., Mahdi, J.G., Taylor, I.N., and Wright, M.A. (1995) J. Chem. Soc., Chem. Commun., 729-730.
199. Kelly, D.R., Knowles, C.J., Mahdi, J.G., Wright, M.A., Taylor, I.N., Hibbs, D.E., Hursthouse, M.B., Mish'al, A.K., Roberts, S.M., Wan, P.W.H., Grogan, G., and Willets, A.J. (1995) J. Chem. Soc., Perkin Trans. 1, 2057-2066.
200. Sandy, H. and Willetts, A.J. (1989) Biotechnol. Lett., 2, 615-620.
201. Bes, M.T., Villa, R., Roberts, S.M.,Wan, P.W.H., and Willetts, A.J. (1996) J. Mol. Catal. B: Enzym., 1, 127-134.
202. Wang, S., Kayser, M.M., and Jurkauskas, V. (2003) J. Org. Chem., 68, 6222-6228.
203. Bradshaw, W.H., Conrad, H.E., Corey, E.J., Gunsalus, I.C., and Lednicer, D. (1959) J. Am. Chem. Soc., 81, 5507.
204. Ougham, H.J., Taylor, D.G. and Trudgill, P.W. (1983) J. Bacteriol., 153, 140-152.
205. Taylor, D.G. and Trudgill, P.W. (1986) J. Bacteriol., 165, 489-497.
206. Jones, K.H., Smith, R.T., and Trudgill, P.W. (1993) J. Gen. Microbiol., 139, 797-805.
207. Taschner, M.J. and Black, D.J. (1988) J. Am. Chem. Soc., 110, 6892-6893.
208. Ottolina, G., de Gonzalo, G., Carrea, G., and Danieli, B. (2005) Adv. Synth. Catal., 347, 1035-1040.
209. Taschner, M.J. and Aminbhavi, A.S. (1989) Tetrahedron Lett., 30, 1029-1032.
210. Yokokawa, F.,Hamada, Y., and Shioiri, T. (1996) Chem. Commun., 871-872.
211. Duchamp, D.J., Branfman, A.R., Button, A.C., and Rinehart, K.L. (1973) J. Am. Chem. Soc., 95, 4077-4078.
212. Bode, J.W., Doyle, M.P., Protopopova, M.N., and Zhou, Q.-L. (1996) J. Org. Chem., 61, 9146-9155.
213. Mazzini, C., Lebreton, J., Alphand,V., and Furstoss, R. (1997) Tetrahedron Lett., 38, 1195-1196.
214. Mazzini, C., Lebreton, J., Alphand,V., and Furstoss, R. (1997) J. Org. Chem., 62, 5215-5218.
215. Mihovilovic, M.D., Muller, B., Kayser, M.M., and Stanetty, P. (2002) Synlett, 700-702.
216. Braun, I., Rudroff, F., Mihovilovic, M.D., and Bach, T. (2006) Angew. Chem. Int. Ed., 45, 5541-5543.
217. Mihovilovic, M.D., Grötzl, B., Kandioller, W., Snajdrova, R., Muskotal, A., Bianchi, D.A., and Stanetty, P. (2006) Adv. Synth. Catal., 348, 463-470.
218. Mihovilovic, M.D., Bianchi, D.A., and Rudroff, F. (2006) Chem. Commun., 3214-3216.
219. Adger, B.M., McCague, R., and Roberts, S.M. (1996) Int. Pat. Appl. WO 96/38437; Chem. Abstr. 126 (1997) 89208.
220. Alphand, V., Archelas, A., and Furstoss, R. (1990) J. Org. Chem., 55, 347-350.
221. Alphand, V., Archelas, A., and Furstoss, R. (1989) Tetrahedron Lett., 30, 3663-3664.
222. Lebreton, J., Alphand, V., and Furstoss, R. (1996) Tetrahedron Lett., 37, 1011-1014.
223. Lebreton, J., Alphand, V., and Furstoss, R. (1997) Tetrahedron, 53, 145-160.
224. Andrau, L., Lebreton, J., Viazzo, P., Alphand, V., and Furstoss, R. (1997) Tetrahedron Lett., 38, 825-826.
225. Gagnon, R., Grogan, G., Levitt, M.S., Roberts, S.M.,Wan, P.W.H., and Willetts, A.J. (1994) J. Chem. Soc., Perkin Trans. 1, 2537-2543.
226. Gagnon, R., Grogan, G., Roberts, S.M., Villa, R., and Willetts, A.J. (1995) J. Chem. Soc., Perkin Trans. 1, 1505-1511.
227. Petit, F. and Furstoss, R. (1995) Synthesis, 1517-1520.
228. Luna, A.,Gutierrez, M.C., Furstoss, R., and Alphand, V. (2005) Tetrahedron: Asymmetry, 16, 2521.
229. Petit, F. and Furstoss, R. (1993) Tetrahedron: Asymmetry, 4, 1341.
230. Arnold, F.H. (2001) Nature, 409, 253-257.
231. Reetz, M.T. (2009) J. Org. Chem., 74, 5767-5778.
232. Reetz, M.T., Becker, M.H., Klein, H.-W., and Stöckigt, D. (1999) Angew. Chem., 111, 1872-1875.
233. Morley, K.L. and Kazlauskas, R.J. (2005) Trends Biotechnol., 23, 231-237.
234. van den Heuvel, R.H.H., Fraaije, M.W., Ferrer, M., Mattevi, A., and van Berkel, W.J.H. (2000) Proc. Natl. Acad. Sci. USA, 97, 9455-9460.
235. Reetz, M.T., Bocola, M., Carballeira, J.D., Zha, D., and Vogel, A. (2005) Angew. Chem. Int. Ed., 44, 4192-4196.
236. Reetz, M.T., Brunner, B., Schneider, T., Schulz, F., Clouthier, C.M., and Kayser, M.M. (2004) Angew. Chem., 116, 4167-4170.
237. Mihovilovic, M.D., Rudroff, F., Winninger, A., Schneider, T., Schulz, F., and Reetz, M.T. (2006) Org. Lett., 8, 1221-1224.
238. Clouthier, C.M., Kayser, M.M., and Reetz, M.T. (2006) J. Org. Chem., 71, 8431-8437.
239. Torrez Pazmino, D.E., Snajdrova, R., Rial, D.V., Mihovilovic, M.D., and Fraaije, M.W. (2007) Adv. Synth. Catal., 349, 1361-1368.
240. Bocola, M., Schulz, F., Leca, F., Vogel, A., Fraaije, M.W., and Reetz, M.T. (2005) Angew. Chem., 347, 979-986.
241. Reetz, M.T. and Wu, S. (2008) Chem. Commun., 5499-5501.
242. Reetz, M.T. and Wu, S. (2009) J. Am. Chem. Soc., 131, 15424-15432.