Citation: Zihan Lin, Wanzhen Lin, Fa-Jie Chen. Electrochemical Modifications of Native Peptides[J]. University Chemistry, ;2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089 shu

Electrochemical Modifications of Native Peptides

Zihan Lin ¹ ,
Wanzhen Lin ^2,, ,
Fa-Jie Chen ^1,,

1.
College of Chemistry, Fuzhou University, Fuzhou 305108, China;
2.
College of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China

Corresponding author: Wanzhen Lin, Fa-Jie Chen,
Received Date: 24 June 2024
Revised Date: 19 September 2024

The rapid development of peptide therapeutics has sparked interest in the chemical modification of native peptides. Electrochemical modification has emerged as a promising technique, offering distinct advantages over traditional chemical approaches, including mild reaction conditions, high chemo-selectivity, and high atom efficiency, all of which align with the principles of green chemistry. This approach has found widespread applications in organic synthesis, with significant progress observed in recent years regarding its use in the modification of native peptides. In this review, we introduce the latest advancements in the field of electrochemical modifications of native peptides, focusing on experimental protocols, reaction mechanisms and synthetic applications.
- Peptide,
- Electrochemistry,
- Green chemistry,
- Reaction mechanism
1. [1]
  Dang, T.; Süssmuth, R. D. Acc. Chem. Res. 2017, 50, 1566.
2. [2]
  Wang, L.; Wang, N.; Zhang, W.; Cheng, X.; Yan, Z.; Shao, G.; Wang, X.; Wang, R.; Fu, C. Signal Transduct. Target. Ther. 2022, 7, 48.
3. [3]
4. [4]
5. [5]
  Heinis, C.; Winter, G. Curr. Opin. Chem. Biol. 2015, 26, 89.
6. [6]
  Jaroszewicz, W.; Morcinek-Orłowska, J.; Pierzynowska, K.; Gaffke, L.; Węgrzyn, G. FEMS Microbiol. Rev. 2021, 46, 1.
7. [7]
  Ji, X.; Nielsen, A. L.; Heinis, C. Angew. Chem. Int. Ed. 2024, 63, e202308251.
8. [8]
  Muttenthaler, M.; King, G. F.; Adams, D. J.; Alewood, P. F. Nat. Rev. Drug Discov. 2021, 20, 309.
9. [9]
  Rhodes, C. A.; Pei, D. Chem. Eur. J. 2017, 23, 12690.
10. [10]
  Wang, W.; Lorion, M. M.; Shah, J.; Kapdi, A. R.; Ackermann, L. Angew. Chem. Int. Ed. 2018, 57, 14700.
11. [11]
  Raynal, L.; Rose, N. C.; Donald, J. R.; Spicer, C. D. Chem. Eur. J. 2021, 27, 69.
12. [12]
  Tong, H.-R.; Li, B.; Li, G.; He, G.; Chen, G. CCS Chemistry 2021, 3, 1797.
13. [13]
  Okada, Y.; Chiba, K. Curr. Opin. Electrochem. 2024, 45, 101469.
14. [14]
  Mackay, A. S.; Payne, R. J.; Malins, L. R. J. Am. Chem. Soc. 2022, 144, 23.
15. [15]
  Fang, X.; Huang, Y.; Hu, X.; Ruan, Z. Chinese J. Org. Chem. 2024, 44, 903.
16. [16]
  Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72.
17. [17]
  Guo, P.; Ye, K.-Y. Science 2023, 380, 34.
18. [18]
  Shen, T.; Li, Y.-L.; Ye, K.-Y.; Lambert, T. H. Nature 2023, 614, 275.
19. [19]
  Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
20. [20]
21. [21]
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
30. [30]
  Renaud, P.; Seebach, D. Angew. Chem. Int. Ed. 1986, 25, 843.
31. [31]
  Lin, Y.; Malins, L. R. Chem. Sci. 2020, 11, 10752.
32. [32]
  Köckinger, M.; Hanselmann, P.; Roberge, D. M.; Geotti-Bianchini, P.; Kappe, C. O.; Cantillo, D. Green Chem. 2021, 23, 2382.
33. [33]
  Shao, X.; Zheng, Y.; Tian, L.; Martín-Torres, I.; Echavarren, A. M.; Wang, Y. Org. Lett. 2019, 21, 9262.
34. [34]
  Nagahara, S.; Okada, Y.; Kitano, Y.; Chiba, K. Chem. Sci. 2021, 12, 12911.
35. [35]
  Li, Y.; Wang, H.; Zhang, H.; Lei, A. Chin. J. Chem. 2021, 39, 3023.
36. [36]
  Kitada, S.; Takahashi, M.; Yamaguchi, Y.; Okada, Y.; Chiba, K. Org. Lett. 2012, 14, 5960.
37. [37]
  Brabec, V.; Mornstein, V. Biophys. Chem. 1980, 12, 159.
38. [38]
  Alvarez-Dorta, D.; Thobie-Gautier, C.; Croyal, M.; Bouzelha, M.; Mével, M.; Deniaud, D.; Boujtita, M.; Gouin, S. G. J. Am. Chem. Soc. 2018, 140, 17120.
39. [39]
40. [40]
  Sato, S.; Matsumura, M.; Kadonosono, T.; Abe, S.; Ueno, T.; Ueda, H.; Nakamura, H. Bioconjug. Chem. 2020, 31, 1417.
41. [41]
  Song, C.; Liu, K.; Wang, Z.; Ding, B.; Wang, S.; Weng, Y.; Chiang, C.-W.; Lei, A. Chem. Sci. 2019, 10, 7982.
42. [42]
  You, S.; Wang, R.; Ma, C.; Lu, C.; Yang, G.; Liu, L.; Weng, Y.; Gao, M. Org. Chem. Front. 2023, 10, 4606.
43. [43]
  Toyama, E.; Maruyama, K.; Sugai, T.; Kondo, M.; Masaoka, S.; Saitoh, T.; Oisaki, K.; Kanai, M. ChemRxiv. doi: 10.26434/chemrxiv.7795484.v7795481
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