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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074
6. [6]
  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
7. [7]
  Honghong Zhang , Zhen Wei , Derek Hao , Lin Jing , Yuxi Liu , Hongxing Dai , Weiqin Wei , Jiguang Deng . Recent advances in synergistic catalytic valorization of CO₂ and hydrocarbons by heterogeneous catalysis. Acta Physico-Chimica Sinica, 2025, 41(7): 100073-. doi: 10.1016/j.actphy.2025.100073
8. [8]
  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-. doi: 10.3866/PKU.WHXB202406029
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Jiaxing Cai , Wendi Xu , Haoqiang Chi , Qian Liu , Wa Gao , Li Shi , Jingxiang Low , Zhigang Zou , Yong Zhou . 具有0D/2D界面的InOOH/ZnIn₂S₄空心球S型异质结用于增强光催化CO₂转化性能. Acta Physico-Chimica Sinica, 2024, 40(11): 2407002-. doi: 10.3866/PKU.WHXB202407002
13. [13]
  Hui Wang , Abdelkader Labidi , Menghan Ren , Feroz Shaik , Chuanyi Wang . 微观结构调控的g-C₃N₄在光催化NO转化中的最新进展：吸附/活化位点的关键作用. Acta Physico-Chimica Sinica, 2025, 41(5): 100039-. doi: 10.1016/j.actphy.2024.100039
14. [14]
  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-. doi: 10.1016/j.actphy.2025.100067
15. [15]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
16. [16]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
17. [17]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
18. [18]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
19. [19]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
20. [20]
  Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077

Get Citation

PDF

XML

Metrics

PDF Downloads(35)
Abstract views(2664)
HTML views(798)

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