Second Generation Baeyer-Villiger Biocatalysts

Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions

Volumn , Issue , 2009, Pages 339-368

  Alphand, Veronique ^a   Fraaije, Marco W ^b   Mihovilovic, Marko D ^c   Ottolina, Gianluca ^d  

^a AIX MARSEILLE UNIVERSITY   (France)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

^c VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^d CNR   (Italy)

Author keywords

Baeyer Villiger biocatalysts; BVMO; Cyclohexanone monooxygenase from Acinetobacter; Monooxygenases; Phenylacetone monooxygenase

Indexed keywords

EID: 84885967570     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527623839.ch21     Document Type: Chapter

References (135)

1. Baeyer, A. and Villiger, V. (1899) Chemische Berichte, 32, 3625-3633.
2. Krow, G.R. (1993) Organic Reactions, 43, 251-798.
3. Renz, M. and Meunier, B. (1999) European Journal of Organic Chemistry, 737-750.
4. Mihovilovic, M.D., Rudroff, F. and Grötzl, B. (2004) Current Organic Chemistry, 8, 1057-1069.
5. Turfitt, G.E. (1948) Biochemical Journal, 42, 376-383.
6. Prairie, R.L. and Talalay, P. (1963) Biochemistry, 2, 203-208.
7. Forney, F.W. and Markovetz, A.J. (1969) Biochemical and Biophysical Research Communications, 37, 31-38.
8. Conrad, H.E., DuBus, R., Namtvedt, M.J. and Gunsalus, I.C. (1965) Journal of Biological Chemistry, 240, 495-503.
9. Willetts, A. (1997) Trends in Biotechnology, 15, 55-62.
10. Ryerson, C.C., Ballou, D.P. and Walsh, C. (1982) Biochemistry, 21, 2644-2655.
11. Sheng, D., Ballou, D.P. and Massey, V. (2001) Biochemistry, 40, 11156-11167.
12. Malito, E., Alfieri, A., Fraaije, M.W. and Mattevi, A. (2004) Proceedings of the National Academy of Sciences of the United States of America, 101, 13157-13162.
13. Fraaije, M.W., Kamerbeek, N.M., Heidekamp, A.J., Fortin, R. and Janssen, D.B. (2004) Journal of Biological Chemistry, 279, 3354-3360.
14. Fraaije, M.W., Kamerbeek, N.M., van Berkel, W.J.H. and Janssen, D.B. (2002) FEBS Letters, 518, 43-47.
15. Torres Pazmiño, D.E. and Fraaije, M.W. (2007) Future directions, in Future Directions in Biocatalysis (ed. T. Matsuda), Elsevier Science, Tokyo, pp. 107-128.
16. Kamerbeek, N.M., Janssen, D.B., van Berkel, W.J.H. and Fraaije, M.W. (2003) Advanced Synthesis Catalysis, 345, 667-678.
17. Mihovilovic, M.D. (2006) Current Organic Chemistry, 10, 1265-1287.
18. Mihovilovic, M.D., Müller, B. and Stanetty, P. (2002) European Journal of Organic Chemistry, 3711-3730.
19. Stewart, J.D. (1998) Current Organic Chemistry, 2, 195-216.
20. Van Beilen, J.B., Mourlane, F., Seeger, M.A., Kovac, J., Li, Z., Smits, T.H.M., Fritsche, U. and Witholt, B. (2003) Environmental Microbiology, 5, 174-182.
21. Stewart, J.D., Reed, K.W. and Kayser, M.M. (1996) Journal of the Chemical Society-Perkin Transactions 1, 755-757.
22. Chen, G., Kayser, M.M., Mihovilovic, M.D., Mrstik, M.E., Martinez, C.A. and Stewart, J.D. (1999) New Journal of Chemistry, 23, 827-832.
23. Bonsor, D., Butz, S.F., Solomons, J., Grant, S., Fairlamb, I.J.S., Fogg, M.J. and Grogan, G. (2006) Organic & Biomolecular Chemistry, 4, 1252-1260.
24. Snajdrova, R., Grogan, G. and Mihovilovic, M.D. (2006) Bioorganic & Medicinal Chemistry Letters, 16, 4813-4817.
25. Kostichka, K., Thomas, S.M., Gibson, K.J., Nagarajan, V. and Cheng, Q. (2001) Journal of Bacteriology, 183, 6478-6486.
26. Kyte, B.G., Rouviere, P., Cheng, Q. and Stewart, J.D. (2004) Journal of Organic Chemistry, 69, 12-17.
27. Donoghue, N.A., Norris, D.B. and Trudgill, P.W. (1976) European Journal of Biochemistry, 63, 175-192.
28. Chen, Y.-C.J., Peoples, O.P. and Walsh, C.T. (1988) Journal of Bacteriology, 170, 781-789.
29. Stewart, J.D. (1998) Current Organic Chemistry, 2, 195-216.
30. Brzostowicz, P., Walters, D.M., Thomas, S.M., Nagarajan, V. and Rouviere, P.E. (2003) Applied and Environmental Microbiology, 69, 334-342.
31. Cheng, Q., Thomas, S.M., Kostichka, K., Valentine, J.R. and Nagarajan, V. (2000) Journal of Bacteriology, 182, 4744-4751.
32. Mihovilovic, M.D., Rudroff, F., Grötzl, B., Kapitan, P., Snajdrova, R., Rydz, J. and Mach, R. (2005) Angewandte Chemie-International Edition, 44, 3609-3613.
33. Bramucci, M.G., Brzostowicz, P.C., Kostichka, K.N., Nagarajan, V., Rouviere, P.E., Thomas, S.M. (2003) PCT Int. Appl, WO 2003020890.
34. Bramucci, M.G., Brzostowicz, P.C., Kostichka, K.N., Nagarajan, V., Rouviere, P.E., Thomas, S.M. (2003) Chemical Abstracts, 138, 233997.
35. Brzostowicz, P.C., Gibson, K.L., Thomas, S.M., Blasko, M.S. and Rouviere, P.E. (2000) Journal of Bacteriology, 182, 4241-4248.
36. Mihovilovic, M.D., Rudroff, F., Müller, B. and Stanetty, P. (2003) Bioorganic & Medicinal Chemistry Letters, 13, 1479-1482.
37. Iwaki, H., Wang, S., Grosse, S., Bergeron, H., Nagahashi, A., Lertvorachon, J., Yang, J., Konishi, Y., Hasegawa, Y. and Lau, P.C.K. (2006) Applied and Environmental Microbiology, 72, 2707-2720.
38. Griffin, M. and Trudgill, P.W. (1976) European Journal of Biochemistry, 63, 199-209.
39. Iwaki, H., Hasegawa, Y., Lau, P.C.K., Wang, S. and Kayser, M.M. (2002) Applied and Environmental Microbiology, 68, 5681-5684.
40. 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) European Journal of Biochemistry, 268, 2547-2557.
41. Kamerbeek, N.M., Olsthorn, A.J.J., Fraaije, M.W. and Janssen, D.B. (2003) Applied and Environmental Microbiology, 69, 419-426.
42. Mihovilovic, M.D., Kapitan, P., Rydz, J., Rudroff, F., Ogink, F.H. and Fraaije, M.W. (2005) Journal of Molecular Catalysis B: Enzymatic, 32, 135-140.
43. Kirschner, A. and Bornscheuer, U.T. (2006) Angewandte Chemie-International Edition, 45, 7004-7006.
44. Malito, E., Alfieri, A., Fraaije, M.W. and Mattevi, A. (2004) Proceedings of the National Academy of Sciences of the United States of America, 101, 13157-13162.
45. Fraaije, M.W., Wu, J., Neuts, D.P.H., van Hellemond, E.W., Spelberg, J.H.L. and Janssen, D.B. (2005) Applied Microbiology and Biotechnology, 66, 393-400.
46. Fraaije, M.W., Kamerbeek, N.M., Heidekamp, A.J., Fortin, R. and Janssen, D.B. (2004) The Journal of Biological Chemistry, 279, 3354-3360.
47. Rudroff, F., Rydz, J., Ogink, F., Fink, M. and Mihovilovic, M.D. (2007) Advanced Synthesis Catalysis, 349, 1436-1444.
48. Snajdrova, R., Braun, I., Bach, T., Mereiter, K. and Mihovilovic, M.D. (2007) Journal of Organic Chemistry, 72, 9597-9603.
49. Morley, K.L. and Kazlauskas, R.J. (2005) Trends in Biotechnology, 23, 231-237.
50. Fraaije, R.H.H., van den Heuvel, M.W., Ferrer, M., Mattevi, A. and van Berkel, W.J.H. (2000) Proceedings of the National Academy of Sciences of the United States of America, 97, 9455-9460.
51. Bocola, M., Schulz, F., Leca, F., Vogel, A., Fraaije, M.W. and Reetz, M.T. (2005) Advanced Synthesis Catalysis, 347, 979-986.
52. Torres Pazmino, D.E., Snajdrova, R., Rial, D.V., Mihovilovic, M.D. and Fraaije, M.W. (2007) Advanced Synthesis Catalysis, 349, 1361-1368.
53. de Gonzalo, G., Ottolina, G., Zambianchi, F., Fraaije, M.W. and Carrea, G. (2006) Journal of Molecular Catalysis B: Enzymatic, 39, 91-97.
54. Reetz, M.T., Brunner, B., Schneider, T., Schulz, F., Clouthier, C.M. and Kayser, M.M. (2004) Angewandte Chemie-International Edition, 43, 4075-4078.
55. Clouthier, C.M., Kayser, M.M. and Reetz, M.T. (2006) Journal of Organic Chemistry, 71, 8431-8437.
56. Clouthier, C.M. and Kayser, M.M. (2006) Tetrahedron: Asymmetry, 17, 2649-2653.
57. Mihovilovic, M.D., Rudroff, F., Winninger, A., Schneider, T., Schulz, F. and Reetz, M.T. (2006) Organic Letters, 8, 1221-1224.
58. Reetz, M.T., Daligault, F., Brunner, B., Hinrichs, H. and Deege, A. (2004) Angewandte Chemie-International Edition, 43, 4078-4081.
59. Zambianchi, F., Raimondi, S., Pasta, P., Carrea, G., Gaggero, N. and Woodley, J.M. (2004) Journal of Molecular Catalysis B: Enzymatic, 31, 165-171.
60. Gibson, M., Nur-e-alam, M., Lipata, F., Oliveira, M.A. and Rohr, J. (2005) Journal of the American Chemical Society, 127, 17594-17595.
61. Ottolina, G., de Gonzalo, G., Carrea, G. and Danieli, B. (2005) Advanced Synthesis Catalysis, 347, 1035-1040.
62. Latham, J.A. and Walsh, C. (1987) Journal of the American Chemical Society, 109, 3421-3427.
63. Mihovilovic, M.D., Müller, B., Kayser, M.M., Stewart, J.D., Fröhlich, J., Stanetty, P. and Spreitzer, H. (2001) Journal of Molecular Catalysis B: Enzymatic, 11, 349-353.
64. Mihovilovic, M.D., Grötzl, B., Kandioller, W., Muskotal, A., Snajdrova, R., Rudroff, F. and Spreitzer, H. (2008) Chemistry & Biodiversity, 5, 490-498.
65. Colonna, S., Gaggero, N., Carrea, G., Ottolina, G., Pasta, P. and Zambianchi, F. (2002) Tetrahedron Letters, 43, 1797-1799.
66. Rial, D.V., Bianchi, D.A., Kapitanova, P., Lengar, A., van Beilen, J.B. and Mihovilovic, M.D. (2008) European Journal of Organic Chemistry, 1203-1213.
67. Faber, K. (2001) Chemistry-A European Journal, 7, 5004-5010.
68. Berezina, N., Alphand, V. and Furstoss, R. (2002) Tetrahedron: Asymmetry, 13, 1953-1955.
69. Gutiérrez, M.C., Furstoss, R. and Alphand, V. (2005) Advanced Synthesis Catalysis, 347, 1051-1059.
70. Geitner, K., Kirschner, A., Rehdorf, J., Schmidt, M., Mihovilovic, M.D. and Bornscheuer, U.T. (2007) Tetrahedron: Asymmetry, 18, 892-895.
71. Rodriguez, C., de Gonzalo, G., Fraaije, M.W. and Gotor, V. (2007) Tetrahedron: Asymmetry, 18, 1338-1344.
72. Alphand, V. and Furstoss, R. (1992) Journal of Organic Chemistry, 57, 1306-1309.
73. Kelly, D.R., Knowles, C.J., Mahdi, J.G., Taylor, I.N. and Wright, M.A. (1995) Journal of the Chemical Society D-Chemical Communications, 729-730.
74. Mihovilovic, M.D. and Kapitan, P. (2004) Tetrahedron Letters, 45, 2751-2754.
75. Mihovilovic, M.D., Kapitan, P. and Kapitanova, P. (2008) ChemSusChem, 1, 143-148.
76. Bonsor, D., Butz, S.F., Solomons, J., Grant, S., Fairlamb, I.J.S., Fogg, M.J. and Grogan, G. (2006) Organic & Biomolecular Chemistry, 4, 1252-1260.
77. Snajdrova, R., Grogan, G. and Mihovilovic, M.D. (2006) Bioorganic & Medicinal Chemistry Letters, 16, 4813-4817.
78. Cernuchova, P. and Mihovilovic, M.D. (2007) Organic & Biomolecular Chemistry, 5, 1715-1719.
79. Berezina, N., Kozma, E., Furstoss, R. and Alphand, V. (2007) Advanced Synthesis Catalysis, 349, 2049-2053.
80. Alphand, V. and Furstoss, R. (1992) Tetrahedron: Asymmetry, 3, 379-382.
81. Kyte, B.G., Rouviere, P., Cheng, Q. and Stewart, J.D. (2004) Journal of Organic Chemistry, 69, 12-17.
82. Adger, B., Bes, M.T., Grogan, G., McCague, R., Pedragosa-Moreau, S., Roberts, S.M., Villa, R., Wan, P.W.H. and Willetts, A.J. (1995) Journal of the Chemical Society D-Chemical Communications, 1563-1564.
83. 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) Bioorganic and Medicinal Chemistry, 5, 253-261.
84. Alphand, V., Archelas, A. and Furstoss, R. (1990) Journal of Organic Chemistry, 55, 347-350.
85. Alphand, V., Archelas, A. and Furstoss, R. (1989) Tetrahedron Letters, 30, 3663-3664.
86. Lebreton, J., Alphand, V. and Furstoss, R. (1997) Tetrahedron, 53, 145-160.
87. Andrau, L., Lebreton, J., Viazzo, P., Alphand, V. and Furstoss, R. (1997) Tetrahedron Letters, 38, 825-826.
88. Mihovilovic, M.D., Bianchi, D.A. and Rudroff, F. (2006) Chemical Communications, 3214-3216.
89. Braun, I., Rudroff, F., Mihovilovic, M.D. and Bach, T. (2006) Angewandte Chemie-International Edition, 45, 5541-5543.
90. Braun, I., Rudroff, F., Mihovilovic, M.D. and Bach, T. (2007) Synthesis, 3896-3906.
91. Colonna, S., Gaggero, N., Pasta, P. and Ottolina, G. (1996) Chemical Communications, 2303-2307.
92. Colonna, S., Gaggero, N., Carrea, G. and Pasta, P. (1998) Chemical Communications, 415-416.
93. de Gonzalo, G., Torres Pazmiño, D.E., Ottolina, G., Fraaije, M.W. and Carrea, G. (2005) Tetrahedron: Asymmetry, 16, 3077-3083.
94. de Gonzalo, G., Torres Pazmiño, D.E., Ottolina, G., Carrea, M.W. and Fraaije, G. (2006) Tetrahedron: Asymmetry, 17, 130-135.
95. Zambianchi, F., Fraaije, M.W., Carrea, G., de Gonzalo, G., Rodríguez, C., Gotor, V. and Ottolina, G. (2007) Advanced Synthesis Catalysis, 349, 1327-1331.
96. Alphand, V., Carrea, G., Wohlgemuth, R., Furstoss, R. and Woodley, J.M. (2003) Trends in Biotechnology, 21, 318-323.
97. Wohlgemuth, R. (2006) Engineering in Life Sciences, 6, 577-583.
98. Law, H.E.M., Baldwin, C.V.F., Chen, B.H. and Woodley, J.M. (2006) Chemical Engineering Science, 61, 6646-6652.
99. van Beilen, J.B., Duetz, W.A., Schmid, A. and Witholt, B. (2003) Trends in Biotechnology, 21, 170-177.
100. Doig, S.D., Simpson, H., Alphand, V., Furstoss, R. and Woodley, J.M. (2003) Enzyme and Microbial Technology, 32, 347-355.
101. Rudroff, F., Alphand, V., Furstoss, R. and Mihovilovic, M.D. (2006) Organic Process Research & Development, 10, 599-604.
102. Walton, A.Z. and Stewart, J.D. (2002) Biotechnology Progress, 18, 262-268.
103. Walton, A.Z. and Stewart, J.D. (2004) Biotechnology Progress, 20, 403-411.
104. Simpson, H., Alphand, V. and Furstoss, R. (2001) Journal of Molecular Catalysis B: Enzymatic, 16, 101-108.
105. Doig, S.D., Avenell, P.J., Bird, P.A., Gallati, P., Lander, K.S., Lye, G.J., Wohlgemuth, R. and Woodley, J.M. (2002) Biotechnology Progress, 18, 1039-1046.
106. Schulz, F., Leca, F., Hollmann, F., Reetz, M.T. and Beilst, J. (2005) Organic Chemistry, 1, 10.
107. Brosa, C., Rodriguez-Santamarta, C., Salva, J. and Barbera, E. (1998) Tetrahedron, 54, 5781-5788.
108. Sometimes called extractive biocatalysis. It was also successfully applied to ketone reduction Vicenzi, J.T., Zmijewski, M.J., Reinhard, M.R., Landen, B.E., Muth, W.L. and Marier, P.G. (1997) Enzyme and Microbial Technology, 20, 494-499.
109. D'Arrigo, P., Lattanzio, M., Fantoni, G.P. and Servi, S. (1998) Tetrahedron: Asymmetry, 9, 4021-4026.
110. Shorrock, V.J., Chartrain, M. and Woodley, J.M. (2004) Tetrahedron, 60, 781-788.
111. Hilker, I., Alphand, V., Wohlgemuth, R. and Furstoss, R. (2004) Advanced Synthesis Catalysis, 346, 203-214.
112. Hilker, I., Gutierrez, M.C., Alphand, V., Wohlgemuth, R. and Furstoss, R. (2004) Organic Letters, 6, 1955-1958.
113. Cells kept at +4°C were still active after several weeks. Berezina, N., Kozma, E., Furstoss, R. and Alphand, V. (2007) Advanced Synthesis Catalysis, 439, 2049-2053.
114. Hilker, I., Baldwin, C., Alphand, V., Furstoss, R., Woodley, J. and Wohlgemuth, R. (2006) Biotechnology and Bioengineering, 93, 1138-1144.
115. Baldwin, C.V.F. and Woodley, J.M. (2006) Biotechnology and Bioengineering, 95, 362-369.
116. Hilker, I., Wohlgemuth, R., Alphand, V. and Furstoss, R. (2005) Biotechnology and Bioengineering, 92, 702-710.
117. Zambianchi, F., Raimondi, S., Pasta, P., Carrea, G., Gaggero, N. and Woodley, J.M. (2004) Journal of Molecular Catalysis B: Enzymatic, 31, 165-171.
118. Zambianchi, F., Pasta, P., Carrea, G., Colonna, S., Gaggero, N. and Woodley, J. M. (2002) Biotechnology and Bioengineering, 78, 489-496.
119. Abril, O., Ryerson, C.C., Walsh, C. and Whitesides, G.M. (1989) Bioorganic Chemistry, 17, 41-52.
120. Zambianchi, F., Pasta, P., Carrea, G., Colonna, S., Gaggero, N. and Woodley, J. M. (2002) Biotechnology and Bioengineering, 78, 489-496.
121. Atia, K.S. (2005) Radiation Physics and Chemistry, 73, 91-99.
122. Recent reviews: Stahl, S., Hober, S., Nilsson, J., Uhlen, M. and Hygren, P.-A. (2003) Biotechnology and Bioengineering, 27, 95-129.
123. Trejo, F., Gelpi, J.L., Busquets, M. and Cortes, A. (1999) Current Topics in Peptide and Protein Research, 3, 173-180.
124. Examples from the recent literature: Narita, J., Okano, K., Tateno, T., Tanino, T., Sewaki, T., Sung, M.-H., Fukuda, H. and Kondo, A. (2006) Applied Microbiology and Biotechnology, 70, 564-572.
125. Giridhar, P.-H., Wu, R. and Wu, W.-T. (2006) Biotechnology and Bioengineering, 95, 1138-1147.
126. Liu, D., Schmid, R.D. and Rusnak, M. (2006) Applied Microbiology and Biotechnology, 72, 1024-1032.
127. Zhan, Y., Li, S.-Z., Li, J., Pan, X., Cahoon, R.E., Jaworski, J.G., Wang, X., Jez, J.M., Chen, F. and Yu, O. (2006) Journal of the American Chemical Society, 128, 13030-13031.
128. Khang, Y.H., Kim, I.W., Hah, Y.R., Hwangbo, J.H. and Kang, K.K. (2003) Biotechnology and Bioengineering, 82, 480-488.
129. Chen, X., Liu, Z., Wang, J., Fang, J., Fan, H. and Wang, P.G. (2000) Journal of Biological Chemistry, 275, 31594-31600.
130. Metcalf, W.W. and Wolfe, R.S. (1998) Journal of Bacteriology, 180, 5547-5558.
131. Garcia Costas, A.M., White, A.K. and Metcalf, W.W. (2001) Journal of Biological Chemistry, 276, 17429-17436.
132. Vrtis, J.M., White, A.K., Metcalf, W.W. and van der Donk, W.A. (2002) Angewandte Chemie, 114, 3391-3393.
133. Vrtis, J.M., White, A.K., Metcalf, W. W. and van der Donk, W.A. (2002) Angewandte Chemie-International Edition, 41, 3257-3259.
134. Woodyer, R.D., van der Donk, W.A. and Zhao, H. (2003) Biochemistry, 42, 11604-11614.
135. Pazmino, D.E.T., Snajdrova, R., Baas, B.-J., Ghobrial, M., Mihovilovic, M.D. and Fraaije, M.W. (2008) Angewandte Chemie-International Edition, 47, 2275-2278.