Biocatalytic reduction of carbonyl groups

Current Organic Chemistry

Volumn 10, Issue 11, 2006, Pages 1217-1246

  Nakamura, Kaoru ^a   Matsuda, Tomoko ^b  

^a KYOTO UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Cofactor regenerating enzymes; Geotrichum candidum; Glutathione S transferase (GST); Molecular hydrogen; Overexpression; Redox reaction

Indexed keywords

CARBONYL COMPOUNDS; ENANTIOSELECTIVITY; HYDROGEN; REDOX REACTIONS;

% REDUCTIONS; ASYMMETRIC REDUCTION; CARBONYL GROUPS; COFACTOR-REGENERATING ENZYME; COFACTORS; GEOTRICHUM CANDIDUM; GLUTATHIONE S-TRANSFERASE; GLUTATHIONE S-TRANSFERASES; MOLECULAR HYDROGEN; OVEREXPRESSIONS;

ENZYMES;

2 CHLORO 1 (3 CHLOROPHENYL)ETHANOL; 4 CHLORO 3 HYDROXY BUTANOATE; 6 BROMOTETRALONE; ACETOPHENONE DERIVATIVE; ALCOHOL DEHYDROGENASE; ALCOHOL DERIVATIVE; ATAZANAVIR; BETA 2 ADRENERGIC RECEPTOR STIMULATING AGENT; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BUTYRIC ACID ETHYL ESTER; CARBONYL DERIVATIVE; CARBONYL REDUCTASE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; FORMIC ACID DERIVATIVE; INDINAVIR; KETONE DERIVATIVE; N TERT BUTYLOXYCARBONYL(BOC) 3 PROLIDINOL; NICOTINAMIDE ADENINE DINUCLEOTIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; ORGANIC SOLVENT; OXIDOREDUCTASE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; PHOSPHODIESTERASE IV INHIBITOR; PYRIDINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SALMETEROL; SODIUM; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AQUEOUS SOLUTION; BACTERIAL STRAIN; BIOCATALYST; BIOTECHNOLOGY; COENZYME; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENERGY RESOURCE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME MECHANISM; ENZYME MODIFICATION; ENZYME STABILITY; FUNGAL STRAIN; GENE OVEREXPRESSION; HYDROPHOBICITY; NONHUMAN; OXIDATION REDUCTION REACTION; REDUCTION KINETICS; REVIEW;

EID: 33745784873     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206777698020     Document Type: Review

References (112)

1. Nakamura, K.; Matsuda, T.; "Enzyme-Catalyzed Reduction Reactions" in "Enzyme Catalysis in organic Synthesis" Ed. by Drauz, K.; Waldmann, H.; 2nd ed. Vol. III, Wiley-VCH, Verlag GmbH, Weinheim, 2002, pp.991-1047
2. Nakamura, K.; Matsuda, T.; Harada T. Chirality, 2002, 14, 703-708
3. Nakamura, K.; Yamanaka, R.; Matsuda, T. Harada, T. Tetrahedron: Asymm. 2003, 14, 2659-2681.
4. Kaluzna, I.; Andrew, A. A.; Bonilla, M.; Martzen, M. R.; Stewart, J. D. J. Mol. Cat. B: Enz. 2002, 17, 101-105
5. Kaluzna, I. A.; Matsuda, T.; Sewell, A. K.; Stewart, J. D. J. Am. Chem. Soc. 2004, 126, 12827-12832.
6. Homann, M. J.; Vail, R. B.; Previte, E.; Tamarez, M.; Morgan, B.; Dodds, D. R.; Zaks, A. Tetrahedron, 2004, 60, 789-797
7. Carballeira, J. D.; Álvarez, E.; Campillo, M.; Pardo, L.; Sinisterra, J. V. Tetrahedron: Asymm. 2004, 15, 951-962
8. Kambourakis, S.; Rozzell, J. D. Tetrahedron, 2004, 60, 663-669.
9. Tsukiji, S.; Pattnaik, S. B.; Suga, H. Nature Structural Biology, 2003, 10, 713-717.
10. Yoshizumi, A.; Wada, M.; Takagi, H.; Shimizu, S.; Nakamori, S. Biosci. Biotechnol. Biochem. 2001, 65, 830-836
11. Patel, R. N. et al. Tetrahedron: Asymm. 2004, 15, 1247-1258
12. Yamamoto, H.; Matsuyama, A.; Kobayashi, Y. Biosci. Biotech. Biochem. 2002, 66, 481-483
13. Yamamoto, H.; Kimoto, N.; Matsuyama, A.; Kobayashi, Y. Biosci. Biotech. Biochem. 2002, 66, 1775-1778.
14. Kataoka, M.; Kita, K.; Wada, M.; Yasohara, Y.; Hasegawa, J.; Shimizu, S. Appl. Microbiol. Biotechnol. 2003, 62, 437-445
15. Yasohara, Y.; Kizaki, N.; Hasegawa, J.; Wada, M.; Kataoka, M.; Shimizu, S. Biosci. Biotechnol. Biochem. 2000, 64, 1430-1436
16. Kizaki, N.; Yasohara, Y.; Hasegawa, J.; Wada, M.; Kataoka, M.; Shimizu, S. Appl. Microbiol. Biotechnol. 2001, 55, 590-595
17. Yasohara, Y.; Kizaki, N.; Hasegawa, J.; Wada, M.; Kataoka, M.; Shimizu, S, Tetrahydron Asymm. 2001, 12, 1713-1718.
18. Allen, S. J.; Holbrook, J. J. Protein Eng. 2000, 13, 5-7.
19. van der Donk, W. A.; Zhao, H. Cur. Opin. Biotechnol. 2003, 14, 421-426.
20. Matsuda, T.; Harada, T.; Nakajima, N.; Nakamura, K. Tetrahedron Lett. 2000, 41, 4135-4138
21. Nakamura, K.; Kitano, K.; Matsuda, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 1629-1632
22. Nakamura, K.; Matsuda, T. J. Org. Chem. 1998, 63, 8957-8964
23. van Deursen, R.; Stampfer, W.; Edegger, K.; Faber, K.; Kroutil, W. J. Mol. Cat. B: Enz. 2004, 31, 159-163
24. Panza, J. L.; Russell, A. J.; Beckman, E. J. Tetrahedron, 2002, 58, 4091-4104.
25. Iyer, R. B.; Bachas, L. G. J. Mol. Cat. B: Enz. 2004, 28, 1-5.
26. Gröger, H.; Hummel, W.; Rollmann, C.; Chamouleau, F.; Hüsken, H.; Werner, H.; Wunderlich, C.; Abokitse, K.; Drauz, K.; Buchholz, S. Tetrahedron, 2004, 60, 633-640
27. Shorrock, V. J.; Chartrain, M.; Woodley, J. M. Tetrahedron, 2004, 60, 781-788.
28. Mertens, R.; Greiner, L.; van den Ban, E. C. D.; Haaker, H. B. C. M. Liese, A. J. Mol. Cat. B: Enz. 2003, 24-25, 39-52
29. Williams, P.; Micklefield, J.; Gardiner, J. M.;Stephens, G. Tetrahedron, 2004, 60, 753-758
30. Wagenknecht, P. S.; Penney, J. M.; Hembre, R. T. Organometallics, 2003, 22, 1180-1182.
31. Nakamura, K.; Yamanaka, R.; Tohi, K.; Hamada, H. Tetrahedron Lett. 2000, 41, 6799-6802
32. Nakamura, K.; Yamanaka, R. Chem. Commun. 2002, 1782-1783
33. Nakamura, K.; Yamanaka, R. Tetrahedron: Asymm. 2002, 13, 2529-2533
34. Parkinson, B. A.; Weaver, P. F. Nature 1984, 309, 148-149
35. Miyatani, R.; Amao, Y. J. Mol. Cat. B: Enz. 2004, 27, 121-125.
36. Kim, S.; Yun, S.-E.; Kang, C. J. Electroanal. Chem. 1999, 465, 153-159
37. Hollmann, F.; Schmid, A.; Steckhan, E. Angew. Chem. Int. Engl. 2001, 40, 169-171
38. Délécouls-Servat, K.; Bergel, A.; Basséguy, R. J. Appl. Electrochem. 2001, 31, 1095-1101
39. Delecouls-Servat, K.; Bergel, A.; Basseguy, R. Biopro. Biosys. Eng. 2004, 26, 205-215
40. Délécouls-Servat, K.; Basséguy, R.; Bergel, A. Chem. Engin. Sci. 2002, 57, 4633-4642
41. Suye, S.; Aramoto, Y.; Nakamura, M.; Tabata, I.; Sakakibara, M. Enzyme Microb. Technol. 2002, 30, 139-144.
42. Nakamura, K.; Inoue, Y.; Matsuda, T.; Misawa, I. J. Chem. Soc. Perkin Trans. 1 1999, 2397-2402
43. Oda, S.; Sugai, T.; Ohta, H. J. Biosci. Bioeng. 2001, 91, 178-183
44. Oda, S.; Sugai, T.; Ohta, H. J. Biosci. Bioeng. 2001, 91, 202-207.
45. Nakamura, K.; Fujii, M.; Ida, Y. J. Chem. Soc. Perkin I, 2000, 3205-3211
46. Kometani, T.; Toide, H.; Daikaiji, Y.; Goto. M. J. Biosci. Bioeng. 2001, 91, 525-527
47. Andrade Conceição, G. J.; Moran, P. J. S.; Rodrigues, J. A. R. Tetrahedron: Asymm. 2003, 14, 43-45.
48. Matsuda, T.; Harada, T.; Nakamura, K. Chem. Commun. 2000, 1367-1368
49. Matsuda, T.; Watanabe, K.; Kamitanaka, T.; Harada, T.; Nakamura, K. Chem. Commun. 2003, 1198-1199.
50. Howarth, J.; James, P.; Dai, J. F. Tetrahedron Lett. 2001, 42, 7517-7519.
51. Matsuda, T.; Nakajima, Y.; Harada, T.; Nakamura K. Tetrahedron: Asymm. 2002, 13, 971-974
52. Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730
53. Matsuda, T.; Harada, T.; Nakajima, N.; Itoh, T.; Nakamura, K. J. Org. Chem. 2000, 65, 157-163
54. Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron, 1998, 54, 8393-8402
55. Nakamura, K.; Takenaka, K.; Fuji, M.; Ida, Y. Tetrahedron Lett. 2002, 43, 3629-3631.
56. Nakamura, K.; Kawai, Y.; Nakajima, N.; Ohno, A. J. Org. Chem. 1991, 56, 4778-4783
57. Ema, T.; Moriya, H.; Kofukuda, T.; Ishida, T.; Maehara, K.; Utaka, M.; Sakai, T. J. Org.Chem. 2001, 6, 8682-8684
58. Manzocchi, A.; Fiecchi, A. Santaniello, S. J. Org. Chem. 1988, 53, 4405-4407
59. Wei, Z.-L.; Lin, G.-Q.; Li, Z.-Y. Bioorg. Med. Chem. 2000, 8, 1129-1137
60. Paizsa, C.; Tosa, M.; Majdik, C.; Moldovan, P.; Novák L.; Kolonits, P. Marcovici, A.; Irimie, F.-D.; Poppe, L. Tetrahedron: Asymm. 2003, 14, 1495-1501.
61. Schubert, T.; Hummel, W.; Kula, M. R.; Müller, M. Eur. J. Org. Chem. 2001, 4181-4187.
62. Itoh, N.; Matsuda, M.; Mabuchi, M.; Dairi, T.; Wang, J. Eur. J. Biochem. 2002, 269, 2394-2402.
63. Stampfer, W.; Kosjek, B.; Faber, K.; Kroutil, W. J. Org. Chem. 2003, 68, 402-406
64. Kosjek, B.; Stampfer, W.; van Deursen, R.; Faber, K.; Kroutil, W. Tetrahedron, 2003, 59, 9517-9521.
65. Dehli, J. R.; Gotor, V. Tetrahedron: Asymm. 2001, 12, 1485-1492
66. Hage, A.; Petra, D. G. I.; Field, J. A.; Schipper, D.; Wijnberg, J. B. P. A.; Kamer, P. C. J.; Reek, J. N. H.; van Leeuwen, P. W. N. M.; Wever, R.; Schoemaker, H. E. Tetrahedron: Asymm. 2001, 12, 1025-1034.
67. Baldassarre, F.; Bertoni, G.; Chiappe, C.; Marion, F. J. Mol. Cat. B: Enz. 2000, 11, 55-58
68. Baskar, B.; Ganesh, S.; Lokeswari, T. S.; Chadha, A. J. Mol. Cat. B: Enz. 2004 27, 13-17
69. Yadav, J. S.; Nanda, S.; Reddy, P. T.; Rao, A. B. J. Org. Chem. 2002, 67, 3900-3903
70. Mczka, W. K.; Mironowicz, A. Tetrahedron: Asymm. 2004, 15, 1965-1967.
71. Kawano, S.; Horikawa, N.; Yasohara, Y.; Hasegawa, J. Biosci. Biotech. Biochem. 2003, 67, 809-814
72. Comasseto, J. V.; Omori, Á. T.; Andrade, L. H.; Porto, A. L. M. Tetrahedron: Asymm. 2003, 14, 711-715
73. Mandal, D.; Ahmad, A.; Khan, M. I.; Kumar, R. J. Mol. Cat. B: Enz. 2004, 27, 61-63.
74. Shimada, H.; Fujiki, S.; Oginuma, M.; Asakawa, M.; Okawara, T.; Kato, K.; Yamamura, S.; Akita, H.; Hara, A.; Imamura, Y. J. Mol. Cat. B: Enz. 2003, 23, 29-35
75. Takemoto, M.; Tanaka, K. J. Mol. Cat. B: Enz. 2001, 15, 173-176
76. Chartrain, M.; Lynch, J.; Choi, W.-B.; Churchill, H.; Patel, S.; Yamazaki, S.; Volante, R.; Greasham, R. J. Mol. Cat. B: Enz. 2000, 8, 285-288.
77. Luo, D.-H.; Zong, M.-H.; Xu, J.-H. J. Mol. Cat. B: Enz. 2003, 24-25, 83-88
78. Lou, W. Y.; Zong, M. H.; Zhang, Y. Y.; Wu, H. Enz. Microb. Technol. 2004, 35, 190-196
79. Zani, P. J. Mol. Cat. B: Enz. 2001, 11, 279-285
80. Andrade, L. H.; Omori, Á. T.; Porto, A. L. M.; Comasseto, J. V. J. Mol. Cat. B: Enz. 2004, 29, 47-54.
81. Lagos, F. M.; Carballeira, J. D.; Bermúdez, J. L.; Alvarez, E.; Sinisterra, J. V. Tetrahedron: Asymm. 2004, 15, 763-770
82. Procopiou, P. A.; Morton, G. E.; Todd, M.; Webb, G. Tetrahedon: Asymm. 2001, 12, 2005-2008
83. Patel, R. N.; Chu, L.; Mueller, R. Tetrahedron: Asymm. 2003, 14, 3105-3109.
84. Haberland, J.; Kriegesmann, A.; Wolfram, E.; Hummel, W.; Liese, A. Appl. Microbiol. Biotechnol. 2002, 58, 595-599
85. Andrade Conceição, G. J.; Moran, P. J. S.; Rodrigues, J. A. R. Tetrahedron: Asymm. 2003, 14, 2327-2330
86. Botes, A.L.; Harvig, D.; van Dyk, M. S.; Sarvary, I; Frejd, T.; Katz, M.; Hahn-Hagerdal, B.; Gorwa-Grauslund, M. F. J. Chem. Soc. Perkin 1, 2002, 1111-1114
87. Katz, M.; Sarvary, I.; Frejd, T.; Hahn-Hagerdal, B.; Gorwa-Grauslund, M. F. Appl. Microbial. Biotechnol. 2002, 59, 641-648
88. Wei, Z.-L.; Li, Z.-Y.; Lin, G.-Q. Tetrahedron:Asymm. 2001, 12, 229-233
89. Utsukihara, T.; Chai, W.; Kato, N.; Nakamura, K.; Horiuchi, C. A. J. Mol. Cat. B: Enz. 2004, 31, 19-24.
90. Engelking, H.; Pfaller, R.; Wich, G.; Weuster-Botz, D. Tetrahedron: Asymm. 2004, 15, 3591-3593
91. Saratani, Y.; Uheda, E.; Yamamoto, H.; Nishimura, A.; Yoshizako, F. Biosci. Biotech. Biochem. 2001, 65, 1676-1679
92. Salvi N. A.; Chattopadhyay, S. Tetrahedron: Asymm. 2004, 15, 3397-3400
93. Bertau, M. Tetrahedron Lett. 2001, 42, 1267-1268
94. Nakamura, K.; Inoue, K.; Ushio, K.; Oka, S.; Ohno, A. Chem. Lett. 1987, 679-682
95. Fadnavis, N. W.; Radhika, K. R. Tetrahedron: Asymm. 2004, 15, 3443-3447.
96. Patel, R. N.; Chu, L.; Chidambaram, R.; Zhu, J.; Kant, J. Tetrahedron: Asymm. 2002, 13, 349-355
97. Chang, C.Y.; Yang, T. K. Tetrahedron: Asymm. 2003, 14, 2239-2245
98. Drochner, D.; Müller, M. Eur. J. Org. Chem. 2001, 211-215
99. Wolberg, M.; Hummel, W.; Wandrey, C.; Müller, M. Angew. Chem. 2000, 39, 4306-4308
100. Wolberg, M.; Hummel, W.; Müller, M. Chem. Eur. J. 2001, 7, 4562-4571.
101. Ji, A.; Wolberg, M.; Hummel, W.; Wandrey, C.; Müller, M. Chem Commun. 2001, 57-58.
102. Benedetti, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E.; Vicario, M. Tetrahedron: Asymm. 2001, 12, 505-511.
103. Perrone, M. G.; Santandrea, E.; Scilimati, A.; Tortorella, V.; Capitelli, R; Bertolasi, V. Tetrahedron: Asymm. 2004, 15, 3501-3510
104. Perrone, M. G.; Santandrea, E.; Scilimati, A.; Syldatk, C. Tortorella, V.; Capitelli, F.; Bertolasi, V. Tetrahedron: Asymm. 2004, 15, 3511-3517.
105. Speicher, A.; Roeser, H.; Heisel, R. J. Mol. Cat. B: Enz. 2003, 22, 71-77
106. Nakamura, K.; Miyoshi, H.; Sugiyama, T.; Hamada, H. Phytochemistry, 1995, 40, 1419-1420.
107. Fronza, G.; Fuganti, C.; Pinciroli, M. Serra, S. Tetrahedron: Asymm. 2004, 15, 3073-3077
108. Fuganti, C.; Serra, S. J. Chem. Soc. Perkin Trans. 1, 2000, 3758-3764
109. Fuganti, C.; Serra, S. J. Chem. Soc. Perkin Trans. 1, 2000, 97-101
110. Serra, S.; Fuganti, C. Tetrahedron: Asymm. 2001, 12, 2191-2196.
111. Nakamura, K; Fujii, M.; Ida, Y. Tetrahedron: Asymm. 2001, 12, 3147-3153
112. Nakamura, K.; Inoue, Y.; Matsuda, A.; Ohno T. Tetrahedron Lett. 1995, 36, 6263-6266.