Biocatalytic Desymmetrization of Dinitriles in Organic Synthesis
- Corresponding author: Ao Yufei, aoyufe@iccas.ac.cn
Citation:
Ao Yufei, Wang Qiqianga, Wang Dexiana. Biocatalytic Desymmetrization of Dinitriles in Organic Synthesis[J]. Chinese Journal of Organic Chemistry,
;2016, 36(10): 2333-2343.
doi:
10.6023/cjoc201605009
Rappoport, Z.; Patai, S. The Chemistry of Functional Groups, The Chemistry of the Cyano Group, Wiley, London, 1970.
Evgred, D.; Harnett, S. Cyanide Compounds in Biology (Ciba Foundation Symposium 140), Wiley, Chichester, 1998. (b) Jallageas, J.-C.; Arnaud, A.; Galzy, P. Adv. Biochem. Eng. 1980, 12, 1. (c) Legras, J.-L.; Chuzel, G.; Arnaud, A.; Galzy, P. World J. Microbiol. Biotechnol. 1990, 6, 83.
Harper, D. B. Biochem. Soc. Trans. 1976, 4, 502. (b) Harper, D. B. Biochem. J. 1977, 165, 309. (c) Kobayashi, M.; Shimizu, S. FEBS Microbiol Lett. 1994, 120, 217.
Asano, Y.; Tani, Y.; Yamada, H. Agric. Biol. Chem. 1980, 44, 2251. (b) Asano, Y.; Tachibana, Y.; Tani, Y.; Yamada, H. Agric. Biol. Chem. 1982, 46, 1175.
Brenner, C. Curr. Opin. Struct. Biol. 2002, 12, 775. (b) Liu, Z. -Q.; Dong, L. -Z.; Cheng, F.; Xue, Y. -P.; Wang, Y. -S.; Ding, J. -N.; Zheng, Y. -G.; Shen, Y. -C. J. Agric. Food Chem. 2011, 59, 11560.
Mascharak, P. K. Coord. Chem. Rev. 2002, 225, 201. (b) Song, L. Y.; Wang, M. Z.; Shi, J. J.; Xue, Z. Q.; Wang, M. -X.; Qian, S. J. Biochem. Biophy. Res. Commun. 2007, 362, 319.
Fournand, D.; Arnaud, A. J. Appl. Microbiol. 2001, 91, 381. (b) Ohtaki, A.; Murata, K.; Sato, Y.; Noguchi, K.; Miyatake, H.; Dohmae, N.; Yamada, K.; Yohda, M.; Odaka, M. Biochim. Biophys. Acta 2010, 1804, 184.
Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci. Biotechnol. Biochem. 1997, 61, 1419. (b) Martínková, L.; Křen, V. Biocatal. Biotrans. 2002, 20, 73. (c) Banerjee, A.; Sharma, R. Banerjee, U. C. Appl. Microbiol. Biotechnol. 2002, 60, 33. (d) Wang, M.-X. Top. Catal. 2005, 35, 117. (e) Martínková, L.; Uhnáková, B.; Pátek, M.; Nešvera, J.; Křen, V. Rhodococcus. Environ. Int. 2009, 35, 162. (f) Wang, M.-X. Chimia 2009, 63, 331. (g) Prasad, S.; Bhalla, T. C. Biotechnol. Adv. 2010, 28, 725; (h) Velankar, H.; Clarke, K. G.; du Preez, R.; Cowan, D. A.; Burton, S. G. Trends Biotechnol. 2010, 28, 561. (i) Wang, M.-X. Top. Organomet. Chem. 2011, 36, 105. (j) Ramteke, P. W.; Maurice, N. G.; Joseph, B.; Wadher, B. J. Biotechnol. Appl. Biochem. 2013, 60, 459. (k) Wang, M.-X. Acc. Chem. Res. 2015, 48, 602.
Garcia-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313. (b) Palomo, J. M.; Cabrera, Z. Curr. Org. Synth. 2012, 9, 791.
Kakya, H.; Sakai, N.; Yokoyama, M.; Sugai, T.; Ohta, H. Chem. Lett. 1991, 1823.
Crosby, J. A.; Parratt, J. S.; Turner, N. J. Tetrahedron:Asymmetry 1992, 3, 1547. (b) Beard, T.; Cohen, M. A.; Parratt, J. S.; Turner, N. J.; Crosby, J.; Moilliet, N. J. Tetrahedron:Asymmetry 1993, 4, 1085.
Wang, M.-X.; Liu, C.-S.; Li, J.-S. Meth-Cohn, O. Tetrahedron Lett. 2000, 41, 8549. (b) Wang, M.-X.; Liu, C.-S.; Li, J.-S. Tetrahedron:Asymmetry 2002, 12, 3367.
Vink, M. K. S.; Schortinghuis, C. A.; Luten, J.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. J. Org. Chem. 2002, 67, 7869.
Santis, D. G.; Zhu, Z. L.; Greenberg, W. A.; Wong, K.; Chaplin, J.; Hanson, S. R.; Farwell, B.; Nicholson, L. W.; Rand, C. L.; Weiner, D. P.; Robertson, D. E.; Burk, M. J. J. Am. Chem. Soc. 2002, 124, 9024. (b) Santis, D. G.; Wong, K.; Farwell, B.; Chatman, K.; Zhu, Z. L.; Tomlinson, G.; Huang, H.; Tan, X.; Bibbs, L.; Chen, P.; Kretz, K.; Burk, M. J. J. Am. Chem. Soc. 2003, 125, 11476.
Bergeron, S.; Chaplin, D. A.; Edwards, J. H.; Ellis, B. S. W.; Hill, C. L.; Karen, H.-T.; Knight, J. R.; Mahoney, T.; Osborne, A. P.; Ruecroft, G. Org. Process Res. Dev. 2006, 10, 661.
Kinfe, H. H.; Chhiba, V.; Frederick, J.; Bode, M. L.; Mathiba, K.; Steenkamp, P. A.; Brady, D. J. Mol. Catal. B:Enzym. 2009, 59. 231.
Duan, Y. T.; Yao, P. Y.; Ren, J.; Han, C.; Li, Q.; Yuan, J.; Feng, J. H.; Wu, Q. Q.; Zhu, D. M. Sci. Chin. Chem. 2014, 57, 1164.
Nojiri, M.; Uekita, K.; Ohnuki, M.; Taoka, N.; Yasohara, Y. J. Appl. Microbiol. 2013, 115, 1127.
Yokoyama, M.; Sugai, T.; Ohta, H. Tetrahedron:Asymmetry 1993, 4, 1081.
Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fuhshuku, K.; Ohta, H.; Sugai, T. Tetrahedron:Asymmetry 2004, 15, 2817.
Wu, Z. -L.; Li, Z. -Y. Chem. Commun. 2003, 386. (b) Wu, Z. -L.; Li, Z. -Y. J. Org. Chem. 2003, 68, 2479. (c) Wu, Z. -L.; Li, Z. -Y. Tetrahedron:Asymmetry 2003, 14, 2133.
Vink, M. K. S.; Wijtmans, R.; Reisinger, C.; Berg, R. J. F.; Schortinghuis, C. A.; Schwab, H.; Schoemaker, H. E.; Rutjes, F. P. J. T. Biotechnol. J. 2006, 1, 569.
Zhang, L.-B.; Wang, D.-X.; Wang, M.-X. Tetrahedron 2011, 67, 5604.
Zhang, L.-B.; Wang, D.-X.; Zhao, L.; Wang, M.-X. J. Org. Chem. 2012, 77, 5584.
Matoishi, K.; Sano, A.; Imai, N.; Yamazaki, T.; Yokoyama, M.; Sugai, T.; Ohta, H. Tetrahedron:Asymmetry 1998, 9, 1097.
Chen, P.; Gao, M.; Wang, D.-X.; Zhao, L.; Wang, M.-X. Chem. Common. 2012, 48, 3482. (b) Chen, P.; Gao, M.; Wang, D.-X.; Zhao, L.; Wang, M.-X. J. Org. Chem. 2012, 77, 4063.
Ao, Y.-F.; Wang, D.-X.; Zhao, L.; Wang, M.-X. Chem. Asian J. 2015, 10, 938.
Kielbasinski, P.; Rachwalski, M.; Mikolajczyk, M.; Szyrej, M.; Wieczorek, M. W.; Wijtmans, R.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2007, 349,1387. (b) Kielbasinski, P.; Rachwalski, M.; Kwiatkowska, M.; Mikolajczyk, M.; Wieczorek, M. W.; Szyrej, M.; Sieron, L.; Rutjes, F. P. J. T. Tetrahedron:Asymmetry 2007, 18, 2108.
Fernandes, B. C. M.; Mateo, C.; Kiziak, C.; Chmura, A.; Wacker, J.; Rantwijk, F. V.; Stolz, A.; Sheldon, R. A. Adv. Synth. Catal. 2006, 348, 2597.
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