Citation: Wang Sheng, Xu Xiaoliang, Li Xiaonian. Progress on the Transformations of Amino Acids by Heterogeneous Catalysis[J]. Chinese Journal of Organic Chemistry, ;2018, 38(3): 565-574. doi: 10.6023/cjoc201709003 shu

Progress on the Transformations of Amino Acids by Heterogeneous Catalysis

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Xu Xiaoliang, xuxiaoliang@zjut.edu.cn; xnli@zjut.edu.cn Li Xiaonian,
Received Date: 4 September 2017
Revised Date: 12 October 2017
Available Online: 3 March 2017
Fund Project: Project supported by the Natural Science Foundation of Zhejiang Province (No. LY18B020018)the Natural Science Foundation of Zhejiang Province LY18B020018

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The catalytic transformation of amino acids is one of the important routes in utilization of amino acids in chemical and biological fields. In this review, catalytic hydrogenation from amino acids to chiral amino alcohols, catalytic decarboxylation to produce amine and nitrile, catalytic deamination to produce carboxylic acid and its derivatives, catalytic pyrolysis to produce bio-fuel and the application as heterogeneous chiral catalyst were summarized. In the catalytic hydrogenation of amino acids, Ru and Rh-based catalysts showed better catalytic performance, and the temperature was a main factor on the optical purity of the product. The decarboxylation, deamination and pyrolysis reaction required relatively high temperature, which needed a large amount of energy consumption. The search of high activity and selectivity heterogeneous catalyst to achieve the reduction of the reaction temperature and pressure is the focus of future research. As the heterogeneous chiral catalyst, the research should be focus on the efficiency, seperation and recycling of the catalyst.
- amino acid,
- heterogeneous catalysis,
- catalytic transformation
1. [1]
2. [2]
  Tuck, C. O.; Pérez, E.; Horváth, I. T.; Sheldon, R. A.; Poliakoff, M. Science 2012, 337, 695. doi: 10.1126/science.1218930
3. [3]
  Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Kesseler, M.; Stürmer, R.; Zelinski, T. Angew. Chem., Int. Ed. 2004, 43, 788. doi: 10.1002/(ISSN)1521-3773
4. [4]
  Demain, A. L. Ind. Biotech. 2007, 3, 269. doi: 10.1089/ind.2007.3.269
5. [5]
  Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. doi: 10.1021/ja00252a056
6. [6]
  Rogers, G. A.; Parsons, S. M.; Anderson, D. C.; Nilsson, L. M.; Bahr, B. A.; Kornreich, W. D.; Kaufman, R.; Jacobs, R. S.; Kirtman, B. J. Med. Chem. 1989, 32, 1217. doi: 10.1021/jm00126a013
7. [7]
  Corey, E. J.; Zhang, F. Y. Angew. Chem., Int. Ed. 1999, 38, 1931. doi: 10.1002/(ISSN)1521-3773
8. [8]
  (a) Abdelrahman, O. A.; Heyden, A.; Bond, J. Q. ACS Catal. 2014, 4, 1171.
  (b) Tan, J.; Cui, J.; Cui, X.; Deng, T.; Li, X.; Zhu, Y.; Li, Y. ACS Catal. 2015, 5, 7379.
  (c) Zhou, M.; Zhang, H.; Ma, H.; Ying, W. Ind. Eng. Chem. Res. 2017, 56, 8833.
9. [9]
  (a) Wang, F.; Zhang, Z. ACS Sustainable Chem. Eng. 2016, 5, 942.
  (b) Adkins, H.; Pavlic, A. A. J. Am. Chem. Soc. 1947, 69, 3039.
  (c) Zhu, Y.; Zhu, Y.; Ding, G.; Zhu, S.; Zheng, H.; Li, Y. Appl. Catal., A 2013, 468, 296.
  (d) Zheng, X.; Lin, H.; Zheng, J.; Duan, X.; Yuan, Y. ACS Catal. 2013, 3, 2738.
10. [10]
  Di, X.; Li, C.; Zhang, B.; Qi, J.; Li, W.; Su, D.; Liang, C. Ind. Eng. Chem. Res. 2017, 56, 4672. doi: 10.1021/acs.iecr.6b04875
11. [11]
  Primo, A.; Concepción, P.; Corma, A. Chem. Commun. 2011, 47, 3613. doi: 10.1039/c0cc05206j
12. [12]
  Fan, G.; Zhou, Y.; Fu, H.; Ye, X.; Li, R.; Chen, H.; Li, X. Chin. J. Chem. 2011, 29, 229. doi: 10.1002/cjoc.201190071
13. [13]
  Adkins, H., Billica, H. R. J. Am. Chem. Soc. 1948, 70, 3121. doi: 10.1021/ja01189a085
14. [14]
  (a) Antons, S.; Beitzke, B. DE 4428106, 1996 [Chem. Abstr. 1996, 124, 288759].
  (b) Antons, S. DE 4444109, 1996 [Chem. Abstr. 1996, 125, 114175].
15. [15]
  Antons, S.; Tilling, A. S.; Wolters, E. WO 9938838, 1999[Chem. Abstr. 1999, 131, 130283].
16. [16]
  Mägerlein, W.; Dreisbach, C.; Hugl, H.; Tse, M. K.; Klawonn, M.; Bhor, S.; Beller, M. Catal. Today 2007, 121, 140. doi: 10.1016/j.cattod.2006.11.024
17. [17]
  Metkar, P. S.; Scialdone, M. A.; Moloy, K. G. Green Chem. 2014, 16, 4575. doi: 10.1039/C4GC01167H
18. [18]
  Gong, D.-C.; Tu, Z.-Y.; He, H.-H.; Wei, P.; Ou Yang, P.-K. Mod. Chem. Ind. 2007, 27, 151(in Chinese). doi: 10.3321/j.issn:0253-4320.2007.z1.035
19. [19]
  Tamura, M.; Tamura, R.; Takeda, Y.; Nakagawa, Y.; Tomishige, K. Chem. Commun. 2014, 50, 6656. doi: 10.1039/c4cc02675f
20. [20]
  Jere, F. T. Ph.D. Dissertation, Michigan State University, East Lansing, 2003.
21. [21]
  Tamura, M.; Tamura, R.; Takeda, Y.; Nakagawa, Y.; Tomishige, K. Chem.-Eur. J. 2015, 21, 3097. doi: 10.1002/chem.201405769
22. [22]
  Holladay, J. E.; Werpy, T. A.; Muzatko, D. S. In Proceedings of the Twenty-Fifth Symposium on Biotechnology for Fuels and Chemicals Held May 4~7, Breckenridge, Humana Press, Clifton, 2003, pp. 857~869.
23. [23]
  Jere, F. T.; Miller, D. J.; Jackson, J. E. Org. Lett. 2003, 5, 527. doi: 10.1021/ol0274211
24. [24]
  Wang, Y. M.S. Thesis, Tianjin University, Tianjin, 2007(in Chinese).
25. [25]
  He, H.-H. M.S. Thesis, Nanjing Tech University, Nanjing, 2005(in Chinese).
26. [26]
  Zwietering, T. N. Chem. Eng. Sci. 1958, 8, 244. doi: 10.1016/0009-2509(58)85031-9
27. [27]
  Jere, F. T.; Jackson, J. E.; Miller, D. J. Ind. Eng. Chem. Res. 2004, 43, 3297. doi: 10.1021/ie034046n
28. [28]
  Bhandare, S. G.; Vaidya, P. D. Ind. Eng. Chem. Res. 2017, 56, 3797. doi: 10.1021/acs.iecr.6b04406
29. [29]
  Pimparkar, K. P.; Miller, D. J.; Jackson, J. E. Ind. Eng. Chem. Res. 2008, 47, 7648. doi: 10.1021/ie800351x
30. [30]
  Roose, P.; Eller, K.; Henkes, E.; Rossbacher, R.; Höke, H. Amines, Aliphatic in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag, Weinheim, Germany, 2015, pp. 1~55.
31. [31]
  Froidevaux, V.; Negrell, C.; Caillol, S.; Pascault, J. P.; Boutevin, B. Chem. Rev. 2016, 116, 14181. doi: 10.1021/acs.chemrev.6b00486
32. [32]
  De Schouwer, F.; Claes, L.; Claes, N.; Bals, S.; Degrève, J.; De Vos, D. E. Green Chem. 2015, 17, 2263. doi: 10.1039/C4GC02194K
33. [33]
  Verduyckt, J.; Van Hoof, M.; De Schouwer, F.; Wolberg, M.; Kurttepeli, M.; Eloy, P.; Gaigneaux, E. M.; Bals, S.; Kirschhock, C. E. A.; De Vos, D. E. ACS Catal. 2016, 6, 7303. doi: 10.1021/acscatal.6b02561
34. [34]
  Verduyckt, J.; Coeck, R.; De Vos, D. E. ACS Sustainable Chem. Eng. 2017, 5, 3290. doi: 10.1021/acssuschemeng.6b03140
35. [35]
  Claes, L.; Verduyckt, J.; Stassen, I.; Lagrain, B.; De Vos, D. E. Chem. Commun. 2015, 51, 6528. doi: 10.1039/C5CC00181A
36. [36]
  Claes, L.; Matthessen, R.; Rombouts, I.; Stassen, I.; De Baerdemaeker, T.; Depla, D.; Delcour, J. A.; Lagrain, B.; DeVos, D. E. ChemSusChem 2015, 8, 345. doi: 10.1002/cssc.201402801
37. [37]
  De Schouwer, F.; Cuypers, T.; Claes, L.; De Vos, D. E. Green Chem. 2017, 19, 1866. doi: 10.1039/C6GC03222B
38. [38]
  Liu, G.; Wright, M. M.; Zhao, Q.; Brown, R. C.; Wang, K.; Xue, Y. Energy Convers. Manage. 2016, 112, 220. doi: 10.1016/j.enconman.2016.01.024
39. [39]
  Yi, L.; Liu, H.; Lu, G.; Zhang, Q.; Wang, J.; Hu, H.; Yao, H. Energ. Fuel. 2017, 31, 9484. doi: 10.1021/acs.energyfuels.7b01413
40. [40]
  Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. 1971, 10, 496. doi: 10.1002/(ISSN)1521-3773
41. [41]
  List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. doi: 10.1021/ja994280y
42. [42]
  List, B. Tetrahedron 2002, 58, 5573. doi: 10.1016/S0040-4020(02)00516-1
43. [43]
  (a) Wang, J.-Z. M.S. Thesis, Beijing University of Chemical Technology, Beijing, 2011(in Chinese).
  王玖钊, 硕士论文, 北京化工大学, 北京, 2011.
  (b) Gruttadauria, M.; Giacalone, F.; Noto, R. Adv. Synth. Catal. 2009, 351, 33.
  (c) Doyagüez, E. G.; Calderon, F.; Sanchez, F.; FernandezMayoralas, A. J. Org. Chem. 2007, 72, 9353.
44. [44]
  Gao, J.; Liu, J.; Jiang, D.; Xiao, B.; Yang, Q. J. Mol. Catal. A:Chem. 2009, 313, 79. doi: 10.1016/j.molcata.2009.08.005
45. [45]
  An, Z.; Zhang, W.; Shi, H.; He, J. J. Catal. 2006, 241, 319. doi: 10.1016/j.jcat.2006.04.035
46. [46]
  An, Z.; Guo, Y.; Zhao, L.; Li, Z.; He, J. ACS Catal. 2014, 4, 2566. doi: 10.1021/cs500385s
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