Biocatalytic Desymmetrization of Dinitriles in Organic Synthesis

doi:10.6023/cjoc201605009

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2333-2343.DOI: 10.6023/cjoc201605009 Previous Articles Next Articles

Reviews

有机合成中腈的去对称化生物转化反应研究进展

敖宇飞^a,b, 王其强^a, 王德先^a,b

a 中国科学院化学研究所北京分子科学国家实验室中国科学院分子识别与功能重点实验室北京 100190;
b 中国科学院大学北京 100049

收稿日期:2016-05-09 修回日期:2016-06-11 发布日期:2016-06-20
通讯作者: 敖宇飞,E-mail:aoyufe@iccas.ac.cn E-mail:aoyufe@iccas.ac.cn
基金资助:
国家自然科学基金（No.21502202）资助项目.

Biocatalytic Desymmetrization of Dinitriles in Organic Synthesis

Ao Yufei^a,b, Wang Qiqianga^a, Wang Dexiana^a,b

a Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
b University of Chinese Academy of Sciences, Beijing 100049

Received:2016-05-09 Revised:2016-06-11 Published:2016-06-20
Supported by:
Project supported by the National Natural Science Foundation of China (No.21502202).

In comparison with the chemical hydration and hydrolysis of nitriles, which usually involves harsh reaction condi-tions and low selectivity, biocatalytic desymmetrizations of prochiral or meso nitriles are highly efficient, highly enantioselective and environmentally benign. Therefore, biocatalysis and biotransformation has offered an attractive and unique protocol for the enantioselective synthesis of polyfunctionalized organic compounds that are not readily obtainable by other methods. This review summarizes the biocatalytic desymmetrization of prochiral nitriles including glutaronitriles, malonitriles and meso cyclic dinitriles during the past two decades.

Key words: desymmetrization, biotransformations, dinitriles

Cite this article

Ao Yufei, Wang Qiqianga, Wang Dexiana. Biocatalytic Desymmetrization of Dinitriles in Organic Synthesis[J]. Chin. J. Org. Chem., 2016, 36(10): 2333-2343.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Faber, K. Biotransformations in Organic Chemistry, 6th ed., Springer, Berlin, 2011.
[2] Rappoport, Z.; Patai, S. The Chemistry of Functional Groups, The Chemistry of the Cyano Group, Wiley, London, 1970.
[3] (a) 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.
[4] (a) 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.
[5] (a) 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.
[6] (a) 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.
[7] (a) 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.
[8] (a) 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.
[9] (a) Sugai, T.; Yamazaki, T.; Yokoyama, M.; Ohta, H. Biosci. Biotechnol. Biochem. 1997, 61, 1419. (b) Martínková, L.; K?en, 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.; K?en, 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.
[10] (a) Garcia-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313. (b) Palomo, J. M.; Cabrera, Z. Curr. Org. Synth. 2012, 9, 791.
[11] Kakya, H.; Sakai, N.; Yokoyama, M.; Sugai, T.; Ohta, H. Chem. Lett. 1991, 1823.
[12] (a) 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.
[13] (a) 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.
[14] 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.
[15] (a) 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.
[16] 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.
[17] 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.
[18] Xu, M. Z.; Ren, J.; Gong, J. S.; Dong, W. Y.; Wu, Q. Q.; Xu, Z. H.; Zhu, D. M. Chin. J. Biotechnol. 2013, 29, 31(in Chinese). (许美珍, 任杰, 龚劲松, 董文玥, 吴洽庆, 许正宏, 朱敦明, 生物工程学报, 2013, 29, 31.)
[19] 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.
[20] Nojiri, M.; Uekita, K.; Ohnuki, M.; Taoka, N.; Yasohara, Y. J. Appl. Microbiol. 2013, 115, 1127.
[21] Yokoyama, M.; Sugai, T.; Ohta, H. Tetrahedron:Asymmetry 1993, 4, 1081.
[22] Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fuhshuku, K.; Ohta, H.; Sugai, T. Tetrahedron:Asymmetry 2004, 15, 2817.
[23] (a) 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.
[24] 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.
[25] Zhang, L.-B.; Wang, D.-X.; Wang, M.-X. Tetrahedron 2011, 67, 5604.
[26] Zhang, L.-B.; Wang, D.-X.; Zhao, L.; Wang, M.-X. J. Org. Chem. 2012, 77, 5584.
[27] Matoishi, K.; Sano, A.; Imai, N.; Yamazaki, T.; Yokoyama, M.; Sugai, T.; Ohta, H. Tetrahedron:Asymmetry 1998, 9, 1097.
[28] (a) 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.
[29] Ao, Y.-F.; Wang, D.-X.; Zhao, L.; Wang, M.-X. Chem. Asian J. 2015, 10, 938.
[30] (a) 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.
[31] 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.

有机合成中腈的去对称化生物转化反应研究进展

Biocatalytic Desymmetrization of Dinitriles in Organic Synthesis

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[2]	Wei Zhao, Jing Liu, Xiangkui He, Hao Jiang, Liangqiu Lu, Wenjing Xiao. N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2504-2514.
[3]	Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1557-1561.
[4]	Ming-Yu Teng, Tao Han, En-He Huang, Long-Wu Ye. Research Progress on Enantioselective Desymmetrization Reactions Involving Metal Carbenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3295-3301.
[5]	Moran Sun, Leiyang Bai, Junhong Xiang, Hua Yang, Dequan Yu, Hongmin Liu. Desymmetrization Strategy: Synthesis of Right Segment of Ingramycin [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 364-369.
[6]	Wang Cai, Zhou Feng, Zhou Jian. Recent Advances in the Enantioselective Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3065-3077.