REVIEWS

Recent Progress in Electrochemical Modification of Amino Acids and Peptides

  • Xinyue Fang ,
  • Yawen Huang ,
  • Xinwei Hu ,
  • Zhixiong Ruan
Expand
  • School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou 511436

Received date: 2023-10-24

  Revised date: 2023-11-21

  Online published: 2023-12-01

Supported by

National Natural Science Foundation of China(22271067); National Natural Science Foundation of China(22201052); Key-Area Research Project of Guangdong Provincial Department of Education(2022ZDZX2051)

Abstract

With the increasing importance of peptides in the treatment of oncological diseases and biomedical applications, the development and construction of new methods for peptide molecules have become a hot research topic for organic synthetic chemists. As a green and efficient reaction tool, organic electrochemistry has been gradually utilized in the field of organic small molecule synthesis in recent years, and its mild and controllable features are suitable for solving the chemo- and regioselectivity problems of the existing bioconjugation strategies, which provide an important synthetic means for the selective modification of peptide molecules. The electrochemical approaches to amino acids and peptides modification developed in the last five years are reviewed, and the distinct advantages of electrochemical synthesis techniques and its applicability in the development of novel biocompatible methodologies are described.

Cite this article

Xinyue Fang , Yawen Huang , Xinwei Hu , Zhixiong Ruan . Recent Progress in Electrochemical Modification of Amino Acids and Peptides[J]. Chinese Journal of Organic Chemistry, 2024 , 44(3) : 903 -926 . DOI: 10.6023/cjoc202310024

References

[1]
Lau J. L.; Dunn M. K. Bioorg. Med. Chem. 2018, 26, 2700.
[2]
(a) Craik D. J.; Fairlie D. P.; Liras S.; Price D. Chem. Biol. Drug Des. 2013, 81, 136.
[2]
(b) Cooper B. M.; Iegre J.; O'Donovan D. H.; Halvarsson M. ?.; Spring D. R. Chem. Soc. Rev. 2021, 50, 1480.
[2]
(c) Muttenthaler M.; King G. F.; Adams D. J.; Alewood P. F. Nat. Rev. Drug Discov. 2021, 20, 309.
[2]
(d) McCarver S. J.; Qiao J. X.; Carpenter J.; Borzilleri R. M.; Poss M. A.; Eastgate M. D.; Miller M. M.; MacMillan D. W. C. Angew. Chem., Int. Ed. 2017, 56, 728.
[3]
Fosgerau K.; Hoffmann T. Drug Discovery Today 2015, 20, 122.
[4]
(a) Ball Z. T. Acc. Chem. Res. 2013, 46, 560.
[4]
(b) Yi L.; Sun H.; Wu Y. W.; Triola G.; Waldmann H.; Goody R. S. Angew. Chem., Int. Ed. 2010, 122, 9607.
[4]
(c) deGruyter J. N.; Malins L. R.; Baran P. S. Biochemistry 2017, 56, 3863.
[4]
(d) Cravatt B. F.; Wright A. T.; Kozarich J. W. Annu. Rev. Biochem. 2008, 77, 383.
[4]
(e) Luther A.; Bisang C.; Obrecht D. Bioorg. Med. Chem. 2018, 26, 2850.
[4]
(f) Bai Z.; Wang H. Synlett 2020, 31, 199.
[4]
(g) Brimble M. A.; Zhang S.;Rodriguez, L. M. M. D. L.; Li, F. F. Chem. Sci. 2023, 14, 7782.
[4]
(h) Budisa N.; V?ller J.; Koksch B.; Acevedo-Rocha C.; Kubyshkin V.; Agostini F. Angew. Chem., Int. Ed. 2017, 56, 9680.
[4]
(i) Chow H. Y.; Zhang Y.; Matheson E.; Li X. Chem. Rev. 2019, 119, 9971.
[4]
(j) King T. A.; Kandemir J. M.; Walsh S. J.; Spring D. R. Chem. Soc. Rev. 2021, 50, 39.
[4]
(k) Liu J.; Wang P.; Yan Z.; Yan J.; Kenry; Zhu Q. ChemBioChem 2021, 22, 2762.
[4]
(l) Mondal S.; Chowdhury S. Adv. Synth. Catal. 2018, 360, 1884.
[5]
Bottecchia C.; No?l T. Chem.-Eur. J. 2018, 25, 26.
[6]
Noisier A. F.; Brimble M. A. Chem. Rev. 2014, 114, 8775.
[7]
Wang W.; Lorion M. M.; Shah J.; Kapdi A. R.; Ackermann L. Angew. Chem., Int. Ed. 2018, 57, 14700.
[8]
Tong H.-R.; Li B.; Li G.; He G.; Chen G. CCS Chem. 2021, 3, 1797.
[9]
Meyer T. H.; Choi I.; Tian C.; Ackermann L. Chem 2020, 6, 2484.
[10]
Siu J. C.; Fu N.; Lin S. Acc. Chem. Res. 2020, 53, 547.
[11]
Yamamoto K.; Kuriyama M.; Onomura O. Acc. Chem. Res. 2019, 53, 105.
[12]
Ang N. W.; Oliveira J. C.; Ackermann L. Angew. Chem., Int. Ed. 2020, 59, 12842.
[13]
Rosen B.; Werner E. J. Am. Chem. Soc. 2014, 136, 5571.
[14]
Mackay A. S.; Payne R. J.; Malins L. R. J. Am. Chem. Soc. 2021, 144, 23.
[15]
Brabec V.; Mornstein V. Biophys. Chem. 1980, 12, 159.
[16]
(a) Brunelle P.; Rauk A. J. Phys. Chem. 2004, 108, 11032.
[16]
(b) Harriman A. J. Phys. Chem. 1987, 91, 6102.
[16]
(c) Jocelyn P. Eur. J. Biochem. 1967, 2, 327.
[16]
(d) Navaratnam S.; Parsons B. J. Chem. Soc., Faraday Trans. 1998, 94, 2577.
[16]
(e) Wilson G. S.; Glass R. S. J. Inorg. Biochem. 1994, 55, 87.
[17]
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.
[18]
Ban H.; Gavrilyuk J.; Barbas III C. F. J. Am. Chem. Soc. 2010, 132, 1523.
[19]
Ban H.; Nagano M.; Gavrilyuk J.; Hakamata W.; Inokuma T.; Barbas III C. F. Bioconjugate Chem. 2013, 24, 520.
[20]
Jessica F.; Corentin W.; Sylvestre D.; Christian L.; André L. RSC Adv. 2013, 3, 24936.
[21]
(a) Nilo A.; Allan M.; Brogioni B.; Proietti D.; Cattaneo V.; Crotti S.; Sokup S.; Zhai H.; Margarit I.; Berti F. Bioconjugate Chem. 2014, 25, 2105.
[21]
(b) Hu Q.-Y.; Allan M.; Adamo R.; Quinn D.; Zhai H.; Wu G.; Clark K.; Zhou J.; Ortiz S.; Wang B. Chem. Sci. 2013, 4, 3827.
[22]
Bauer D. M.; Ahmed I.; Vigovskaya A.; Fruk L. Bioconjugate Chem. 2013, 24, 1094.
[23]
Madl C. M.; Heilshorn S. C. Bioconjugate Chem. 2017, 28, 724.
[24]
Cui L.; Ma Y.; Li M.; Wei Z.; Huan Y.; Li H.; Fei Q.; Zheng L. Anal. Chem. 2021, 93, 4434.
[25]
Sato, S.; Matsumura, M.; Kadonosono, T.; Abe, S.; Ueno, T.; Ueda, H.; Nakamura, H. Bioconjugate Chem. 2020, 31, 1417.
[26]
Depienne S.; Alvarez-Dorta D.; Croyal M.; Temgoua R. C. T.; Charlier C.; Deniaud D.; Mével M.; Boujtita M.; Gouin S. G. Chem. Sci. 2021, 12, 15374.
[27]
Song C.; Liu K.; Wang Z.; Ding B.; Wang S.; Weng Y.; Chiang C.-W.; Lei A. Chem. Sci. 2019, 10, 7982.
[28]
Stangier M.; Messinis A. M.; Oliveira J. C. A.; Yu H.; Ackermann L. Nat. Commun. 2021, 12, 4736.
[29]
Hou X.; Kaplaneris N.; Yuan B.; Frey J.; Ohyama T.; Messinis A. M.; Ackermann L. Chem. Sci. 2022, 13, 3461.
[30]
You S.; Wang R.; Ma C.; Lu C.; Yang G.; Liu L.; Weng Y.; Gao M. Org. Chem. Front. 2023, 10, 4606.
[31]
Toyama E.; Maruyama K.; Sugai T.; Kondo M.; Masaoka S.; Saitoh T.; Oisaki K.; Kanai M. 2019, 10.26434/ chemrxiv.7795484.v1.
[32]
Seki Y.; Ishiyama T.; Sasaki D.; Abe J.; Sohma Y.; Oisaki K.; Kanai M. J. Am. Chem. Soc. 2016, 138, 10798.
[33]
Wu J.; Abou-Hamdan H.; Guillot R.; Kouklovsky C.; Vincent G. Chem. Commun. 2020, 56, 1713.
[34]
Weng Y.; Xu X.; Chen H.; Zhang Y.; Zhuo X. Angew. Chem., Int. Ed. 2022, 61, e202206308.
[35]
Qiu Y.; Scheremetjew A.; Finger L. H.; Ackermann L. Chem.- Eur. J. 2020, 26, 3241.
[36]
Chen H. C.; Wan C.; Shih W. H.; Kao C. Y.; Jiang H.; Weng Y.; Chiang C. W. Asian J. Org. Chem. 2022, 12, e202200647.
[37]
Kawamata Y.; Vantourout J. C.; Hickey D. P.; Bai P.; Chen L.; Hou Q.; Qiao W.; Barman K.; Edwards M. A.; Garrido-Castro A. F.; deGruyter J. N.; Nakamura H.; Knouse K.; Qin C.; Clay K. J.; Bao D.; Li C.; Starr J. T.; Garcia-Irizarry C.; Sach N.; White H. S.; Neurock M.; Minteer S. D.; Baran P. S. J. Am. Chem. Soc. 2019, 141, 6392.
[38]
Ma Y.; Hong J.; Yao X.; Liu C.; Zhang L.; Fu Y.; Sun M.; Cheng R.; Li Z.; Ye J. Org. Lett. 2021, 23, 9387.
[39]
Novaes L. F. T.; Ho J. S. K.; Mao K.; Liu K.; Tanwar M.; Neurock M.; Villemure E.; Terrett J. A.; Lin S. J. Am. Chem. Soc. 2022, 144, 1187.
[40]
Lamb C. M. G.; Shi J.; Wilden J. D.; Macmillan D. Org. Biomol. Chem. 2022, 20, 7343.
[41]
Mackay A. S.; Maxwell J. W.; Bedding M. J.; Kulkarni S. S.; Byrne S. A.; Kambanis L.; Popescu M. V.; Paton R. S.; Malins L. R.; Ashhurst A. S.; Corcilius L.; Payne R. J. Angew. Chem.,Int. Ed. 2023, e202313037.
[42]
You S.; Ruan M.; Lu C.; Liu L.; Weng Y.; Yang G.; Wang S.; Alhumade H.; Lei A.; Gao M. Chem. Sci. 2022, 13, 2310.
[43]
Liu L.; Xu Z.; Liu T.; Xu C.; Zhang W.; Hua X.; Ling F.; Zhong W. J. Org. Chem. 2022, 87, 11379.
[44]
Wang R.; Wang J.; Zhang Y.; Wang B.; Xia Y.; Xue F.; Jin W.; Liu C. Adv. Synth. Catal. 2023, 365, 900.
[45]
Kawamata Y.; Hayashi K.; Carlson E.; Shaji S.; Waldmann D.; Simmons B. J.; Edwards J. T.; Zapf C. W.; Saito M.; Baran P. S. J. Am. Chem. Soc. 2021, 143, 16580.
[46]
Zeng S.; Fang S.; Cai H.; Wang D.; Liu W.; Hu X.; Sun P.; Ruan Z. Chem. Asian J. 2022, 17, e202200762.
[47]
Qiu Y.; Stangier M.; Meyer T. H.; Oliveira J. C. A.; Ackermann L. Angew. Chem., Int. Ed. 2018, 57, 14179.
[48]
Feng T.; Wang S.; Liu Y.; Liu S.; Qiu Y. Angew. Chem., Int. Ed. 2021, 61, e202115178.
[49]
Li P.; Guo C.; Wang S.; Ma D.; Feng T.; Wang Y.; Qiu Y. Nat. Commun. 2022, 13, 3774.
[50]
Wang Y.; Tang S.; Yang G.; Wang S.; Ma D.; Qiu Y. Angew. Chem., Int. Ed. 2022, 61, e202207746.
[51]
Liang H.; Julaiti Y.; Zhao C.-G.; Xie J. Nat. Synth. 2023, 2, 338.
[52]
Huang H.; Lambert T. H. Angew. Chem., Int. Ed. 2021, 60, 11163.
[53]
Huang H.; Lambert T. H. J. Am. Chem. Soc. 2021, 143, 7247.
[54]
Klocke E.; Matzeit A.; Gockeln M.; Sch?fer H. J. Chem. Ber. 1993, 126, 1623.
[55]
Shao X.; Zheng Y.; Tian L.; Martín-Torres I.; Echavarren A. M.; Wang Y. Org. Lett. 2019, 21, 9262.
[56]
Chen X.; Luo X.; Peng X.; Guo J.; Zai J.; Wang P. Chem. Eur. J. 2020, 26, 3226.
[57]
Barton L. M.; Chen L.; Blackmond D. G.; Baran P. S. Proc. Natl. Acad. Sci. 2021, 118, e2109408118.
[58]
Qin T.; Malins L. R.; Edwards J. T.; Merchant R. R.; Novak A. J.; Zhong J. Z.; Mills R. B.; Yan M.; Yuan C.; Eastgate M. D. Angew. Chem., Int. Ed. 2017, 56, 260.
[59]
McCarver S. J.; Qiao J. X.; Carpenter J.; Borzilleri R. M.; Poss M. A.; Eastgate M. D.; Miller M. M.; MacMillan D. W. Angew. Chem., Int. Ed. 2017, 129, 746.
[60]
K?ckinger M.; Hanselmann P.; Roberge D. M.; Geotti-Bianchini P.; Kappe C. O.; Cantillo D. Green Chem. 2021, 23, 2382.
[61]
Renaud P.; Seebach D. Angew. Chem.,Int. Ed. Engl. 1986, 25, 843.
[62]
Lin Y.; Malins L. R. Chem. Sci. 2020, 11, 10752.
[63]
Lin Y.; Malins L. R. J. Am. Chem. Soc. 2021, 143, 11811.
[64]
Li S.; Li X.; Wang T.; Yang Q.; Ouyang Z.; Chen J.; Zhai H.; Li X.; Cheng B. Adv. Synth. Catal. 2022, 364, 2346.
[65]
Cui J.-F.; Zhong W.-Q.; Huang J.-M. J. Org. Chem. 2023, 88, 1147.
[66]
Lu Y.-H.; Mu S.-Y.; Li H.-X.; Jiang J.; Wu C.; Zhou M.-H.; Ouyang W.-T.; He W.-M. Green Chem. 2023, 25, 5539.
[67]
Gausmann M.; Kreidt N.; Christmann M. Org. Lett. 2023, 25, 2228.
[68]
Li Y.; Wang H.; Zhang H.; Lei A. Chin. J. Chem. 2021, 39, 3023.
[69]
Li C.-J. Acc. Chem. Res. 2009, 42, 335.
[70]
Wang H.; He M.; Li Y.; Zhang H.; Yang D.; Nagasaka M.; Lv Z.; Guan Z.; Cao Y.; Gong F.; Zhou Z.; Zhu J.; Samanta S.; Chowdhury A. D.; Lei A. J. Am. Chem. Soc. 2021, 143, 3628.
[71]
Palma A.; Cárdenas J.; Frontana-Uribe B. A. Green Chem. 2009, 11, 283.
[72]
Nagahara S.; Okada Y.; Kitano Y.; Chiba K. Chem. Sci. 2021, 12, 12911.
[73]
Chiba K.; Kono Y.; Kim S.; Nishimoto K.; Kitano Y.; Tada M. Chem. Commun. 2002, No. 16, 1766.
[74]
(a) Cortes-Clerget M.; Berthon J.-Y.; Krolikiewicz-Renimel I.; Chaisemartin L.; Lipshutz B. H. Green Chem. 2017, 19, 4263.
[74]
(b) Cortes-Clerget M.; Spink S. E.; Gallagher G. P.; Chaisemartin L.; Filaire E.; Berthon J.-Y.; Lipshutz B. H. Green Chem. 2019, 21, 2610.
[74]
(c) Knauer S.; Koch N.; Uth C.; Meusinger R.; Avrutina O.; Kolmar H. Angew. Chem., Int. Ed. 2020, 59, 12984.
[74]
(d) Pawlas J.; Rasmussen J. H. ChemSusChem. 2021, 14, 3231.
Outlines

/