新型酰基供体用于酶法动力学拆分制备(R)-1-(2-萘基)乙胺的研究

doi:10.6023/cjoc1105101

有机化学 ›› 2012, Vol. ›› Issue (03): 526-531.DOI: 10.6023/cjoc1105101 上一篇下一篇

研究论文

新型酰基供体用于酶法动力学拆分制备(R)-1-(2-萘基)乙胺的研究

符思敏, 徐刚, 陈永军, 吴坚平, 杨立荣

浙江大学化学工程与生物工程学系杭州 310027

收稿日期:2011-05-10 修回日期:2011-10-20 发布日期:2012-03-24
通讯作者: 徐刚 E-mail:xugang_1030@zju.edu.cn
基金资助:
国家自然科学基金(Nos. 20606030, 20936002)、国家863 计划(No. 2006AA02Z238)以及国家973 计划(Nos. 2011CB710800, 2009CB724706)资助项目.

Preparation of (R)-1-(2-Naphthyl)ethylamine by Enzymatic Kinetic Resolution with A New Acyl Donor

Fu Simin, Xu Gang, Chen Yongjun, Wu Jianping, Yang Lirong

Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027

Received:2011-05-10 Revised:2011-10-20 Published:2012-03-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20606030, 20936002), the National High-tech Research and Development Program of China (No. 2011AA02A209) and the Major State Basic Research Development Program of China (Nos. 2011CB710800, 2009CB724706).

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摘要/Abstract

首次成功实现了光学纯(R)-1-(2-萘基)乙胺的高效酶法动力学拆分制备, 考察了脂肪酶种类、溶剂、酰基供体、底物浓度、反应温度等对拆分效果的影响, 发现新型酰基供体——正戊酸对氯苯酯能够很好地抑制非酶促自催化酰胺化效应. 在甲苯溶剂中, 底物浓度300 mmol/L, 40 ℃条件下, 采用该供体在脂肪酶Novozym 435 催化下, 动力学拆分反应8 h 转化率达到理论最佳值50%, ee_p＞99%.

关键词: (R)-1-(2-萘基)乙胺, 正戊酸对氯苯酯, Novozym 435, 酶动力学拆分

Enantiomerically pure (R)-1-(2-naphthyl)ethylamine was firstly prepared by an efficient enzymatic kinetic resolution process. The effects of lipases, solvents, acyl donors, substrate concentration and temperature on the reaction were investigated. It was found that as the acyl donor, 4-chlorophenyl valerate could effectively inhibit the non-selective amidation reaction. The optimal solvent, amine concentration and temperature were toluene, 300 mmol/L and 40 ℃, respectively. Under the optimal conditions mentioned above, an excellent ee_p value (＞99%) at high conversion (50%) in 8 h could be achieved on the kinetic resolution reaction catalyzed by Novozym 435 with the new acyl donor.

Key words: (R)-1-(2-naphthyl) ethylamine, 4-chlorophenyl valerate, Novozym 435, enzymatic kinetic resolution

引用此文

符思敏, 徐刚, 陈永军, 吴坚平, 杨立荣. 新型酰基供体用于酶法动力学拆分制备(R)-1-(2-萘基)乙胺的研究[J]. 有机化学, 2012, (03): 526-531.

Fu Simin, Xu Gang, Chen Yongjun, Wu Jianping, Yang Lirong . Preparation of (R)-1-(2-Naphthyl)ethylamine by Enzymatic Kinetic Resolution with A New Acyl Donor[J]. Chin. J. Org. Chem., 2012, (03): 526-531.

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参考文献

[1] Ghosh, A. K.; Takayama, J.; Aubin, Y.; Ratia, K.; Chaudhuri, R.;Baez, Y.; Sleeman, K.; Coughlin, M.; Nichols, D. B.; Mulhearn, D.C.; Prabhakar, B. S.; Baker, S. C.; Johnson, M. E.; Mesecar, A. D.J. Med. Chem. 2009, 52, 5228.

[2] Fredga, A.; Sjoberg, B.; Sandberg, R. Acta Chem. Scand. 1957, 11,1609.

[3] Mereyala, H. B.; Pola, P. Tetrahedron: Asymmetry 2003, 14, 2683.

[4] Shimada, T.; Kobayashi, Y.; Saigo, K. Tetrahedron: Asymmetry2005, 16, 3807.

[5] Hu, J.; Dong, J.; Shi, X.-X. Chin. J. Synth. Chem. 2010, (1), 61 (inChinese).(胡健, 董菁, 施小新, 合成化学, 2010, (1), 61.)

[6] Szatmári, I.; Sillanp??, R.; Fül?p, F. Tetrahedron: Asymmetry 2008,19, 612.

[7] Gül, N.; Nelson, J. H. J. Mol. Struct. 1999, 475, 121.

[8] Pallavicini, M.; Bolchi, C.; Fumagalli, L.; Valoti, E.; Villa, L. Tetrahedron:Asymmetry 2002, 13, 2277.

[9] Mereyala, H. B.; Pola, P. Tetrahedron: Asymmetry 2003, 14, 2683.

[10] Kazuhiko, S.; Yuka, K.; Takanobu. [10] Kazuhiko, S.; Yuka, K.;Takanobu. JP 2005060231, 2005 [Chem. Abstr. 2005, 142,297888].

[11] Guijarro, D.; Pablo, ó.; Yus, M. J. Org. Chem. 2010, 75, 5265.

[12] Kadyrov, R.; Thomas, H. R. Angew. Chem., Int. Ed. 2003, 42,5472.

[13] Savile, C. K.; Janey, J. M.; Mundorff, E. C.; Moore, J. C.; Tam, S.;Jarvis, W. R.; Colbeck, J. C.; Krebber, A.; Fleitz, F. J.; Brands, J.;Devine, P. N.; Huisman, G. W.; Hughes, G. J. Science 2010, 329,305.

[14] Shen, H.-Y.; Tian, G.-L.; Ye, Y.-H. Chin. J. Org. Chem. 2003, 23,221 (in Chinese).(沈鸿雁, 田桂玲, 叶蕴华, 有机化学, 2003, 23, 221.)

[15] Huang, L.-Q.; Chen, D.-W.; Yang, H. Chin. J. Org. Chem. 2005,25, 1575 (in Chinese).(黄丽琴, 陈道文, 杨红, 有机化学, 2005, 25, 1575.)

[16] Jin, Y.; Wu, J.-P.; Xu, G.; Yang, L.-R. Chin. J. Org. Chem. 2006,26, 1384 (in Chinese).(金勇, 吴坚平, 徐刚, 杨立荣, 有机化学, 2006, 26, 1384.)

[17] Xu, G.; Cheng, Y.-M.; Wu, J.-P.; Yang, L.-R. Chin. J. Org. Chem.2007, 27, 857 (in Chinese).(徐刚, 程永梅, 吴坚平, 杨立荣, 有机化学, 2007, 27, 857.)

[18] Wang, M.-H.; Yang, G.; Yang, L.-R. Chin. J. Org. Chem. 2008, 28,1398 (in Chinese).(王明慧, 杨光, 杨立荣, 有机化学, 2008, 28, 1398.)

[19] Wang, S.-Z.; Wu, J.-P.; Xu, G.; Yang, L.-R. Chin. J. Org. Chem.2008, 9, 1584 (in Chinese).(王世珍, 吴坚平, 徐刚, 杨立荣, 有机化学, 2008, 9, 1584.)

[20] Youshko, M. I.; Rantwijk, F. V.; Sheldon, R. A. Tetrahedron:Asymmetry 2001, 12, 3267.

[21] Davis, B. A.; Durden, D. A. Synth. Commun. 2001, 31, 569-578.

[22] Yang, B.; Taeko, I.; Zhang, S.-S. Chem. J. Chin. Univ. 2001, 22,1332 (in Chinese).(杨波, 泉多惠子, 张书圣, 高等学校化学学报, 2001, 22, 1332.)

[23] Xu, G.; Dai, J.-Q.; Wu, J.-P.; Yang, L.-R. J. Chem. Ind. Eng. 2007,58, 1741 (in Chinese). (徐刚, 戴军强, 吴坚平, 杨立荣, 化工学报, 2007, 58, 1741.)

[24] Alexander, E. R.; Misegades, A. L. J. Am. Chem. Soc. 1948, 70,1315.

[25] Malanga, C.; Urso, A.; Lardicci, L. Tetrahedron Lett. 1995, 36,8859.

新型酰基供体用于酶法动力学拆分制备(R)-1-(2-萘基)乙胺的研究

Preparation of (R)-1-(2-Naphthyl)ethylamine by Enzymatic Kinetic Resolution with A New Acyl Donor

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