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

Figures(14)

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
1. [1]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
2. [2]
  Yutong Liu , Xuemin Jing . Research Progress on the Catalytic Conversion of Methane in the Context of the “Dual Carbon” Goals. University Chemistry, 2025, 40(10): 101-113. doi: 10.12461/PKU.DXHX202412018
3. [3]
  Tao Wang , Qin Dong , Cunpu Li , Zidong Wei . Sulfur Cathode Electrocatalysis in Lithium-Sulfur Batteries: A Comprehensive Understanding. Acta Physico-Chimica Sinica, 2024, 40(2): 2303061-0. doi: 10.3866/PKU.WHXB202303061
4. [4]
  Runjie Li , Hang Liu , Xisheng Wang , Wanqun Zhang , Wanqun Hu , Kaiping Yang , Qiang Zhou , Si Liu , Pingping Zhu , Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059
5. [5]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
6. [6]
  Zixuan Zhao , Miao Fan . “Carbon” with No “Ester”: A Boundless Journey of CO₂ Transformation. University Chemistry, 2025, 40(7): 213-217. doi: 10.12461/PKU.DXHX202409040
7. [7]
  Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074
8. [8]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
9. [9]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
10. [10]
  Honghong Zhang , Zhen Wei , Derek Hao , Lin Jing , Yuxi Liu , Hongxing Dai , Weiqin Wei , Jiguang Deng . 非均相催化CO₂与烃类协同催化转化的最新进展. Acta Physico-Chimica Sinica, 2025, 41(7): 100073-0. doi: 10.1016/j.actphy.2025.100073
11. [11]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029
12. [12]
  Yuhang Zhang , Yi Li , Yuehan Cao , Yingjie Shuai , Yu Zhou , Ying Zhou . Regulating the formation type by Ir of intermediates to suppress product overoxidation in photocatalytic methane conversion. Acta Physico-Chimica Sinica, 2026, 42(2): 100173-0. doi: 10.1016/j.actphy.2025.100173
13. [13]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
14. [14]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
15. [15]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
16. [16]
  Shuang Cao , Bo Zhong , Chuanbiao Bie , Bei Cheng , Feiyan Xu . Insights into Photocatalytic Mechanism of H₂ Production Integrated with Organic Transformation over WO₃/Zn_0.5Cd_0.5S S-Scheme Heterojunction. Acta Physico-Chimica Sinica, 2024, 40(5): 2307016-0. doi: 10.3866/PKU.WHXB202307016
17. [17]
  Xinlong XU , Chunxue JING , Yuzhen CHEN . Bimetallic MOF-74 and derivatives: Fabrication and efficient electrocatalytic biomass conversion. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1545-1554. doi: 10.11862/CJIC.20250046
18. [18]
  Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO₂ adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220
19. [19]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
20. [20]
  Yuchen Zhou , Huanmin Liu , Hongxing Li , Xinyu Song , Yonghua Tang , Peng Zhou . Designing thermodynamically stable noble metal single-atom photocatalysts for highly efficient non-oxidative conversion of ethanol into high-purity hydrogen and value-added acetaldehyde. Acta Physico-Chimica Sinica, 2025, 41(6): 100067-0. doi: 10.1016/j.actphy.2025.100067

Get Citation

PDF

XML

Metrics

PDF Downloads(39)
Abstract views(3452)
HTML views(891)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142