Recent Progress in Electrochemical Modification of Amino Acids and Peptides

doi:10.6023/cjoc202310024

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.

Key words: organic electrochemistry, amino acids, peptide modifications, chemo- and regio-selectivity

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 31

Figure 1. Representative peptide drugs

Figure 2. Tyrosine modification of peptides and proteins by electrochemical activation of small-molecule reagents (A) e-Y-click reaction, (B) modified e-Y-click reaction, (C) modification of Trastuzumab

Figure 3. Tyrosine modification of peptides and proteins by electrochemical activation of phenothiazine derivatives

Figure 4. Rhodium-electrocatalyzed cyclization of 2-hydroxybenzaldehyde tyrosine analogues with alkynes

Figure 5. Tyrosine modification of peptides by ruthenium-electrocatalyzed C—H acylation

Figure 6. Electrochemically mediated reaction and mechanism of tyrosine with o-aminobenzoic acid derivatives

Figure 7. Electrochemically-promoted tryptophan-selective bioconjugation of peptides and proteins

Figure 8. Electrochemically mediated halogenation cyclization reaction of tryptophan derivatives

Figure 9. (A) Tryptophan modification of peptides by manganese-electrocatalyzed azide/heterocyclization cascades, (B) stereo configuration, and (C) proposed mechanism

Figure 10. (A) Electrophotocatalyzed trifluoromethylation of tryptophan, and (B) electrochemically mediated trifluoromethylation and mechanism of tryptophan

Figure 11. -1 Nickel-electrocatalyzed C—N cross-coupling reaction of p-bromophenylalanine with amines

Figure 11. -2 Mechanism of C—N cross-coupling reaction between p-bromophenylalanine and amines by nickel-electrocatalyzed

Figure 12. Electrochemically mediated α-methylation of proline

Figure 13. Electrochemically mediated desulfurization and mechanism of cysteine

Figure 14. Electrochemical selenoetherification and mechanism of selenocysteine

Figure 15. Electrochemically mediated cascade annulation and mechanism of serine

Figure 16. Electrochemical modification of glycine (A) Electrochemically mediated intramolecular oxidative cyclization of glycine derivatives, and (B) electrochemically mediated phosphorylation and mechanism of glycine derivatives

Figure 17. Electrochemically mediated reduction of N-terminal phthalimides of peptides

Figure 18. Selenium-electrocatalyzed dehydrocyclization of 2-vinylaromatic amines

Figure 19. (A) Iridium-electrocatalyzed cyclization of olefins with benzoic acid, (B) electrochemical desaturative β-acylation of cyclic N-aryl amines, (C) electrochemically mediated reductive deuteration of alkyl halides, and (D) electrochemically mediated reaction and mechanism of aryl epoxides and carbon dioxide

Figure 20. Gold-electrocatalyzed C(sp)—C(sp2) coupling reaction and mechanism of alkynes with arylhydrazines

Figure 21. (A) Electrophotocatalytic hydroxylation of aromatic hydrocarbons, and (B) electrophotocatalytic acetoxyhydroxylation of olefins

Figure 22. Electrochemically mediated C(sp3)—N decarboxylation coupling reaction of α-amino acids

Figure 23. Electrochemically mediated intramolecular decarboxylative cyclization of heptapeptide

Figure 24. Electrochemically mediated decarboxylative acetoxylation of amino acids

Figure 25. Electrochemically mediated decarboxylation of peptides for late-stage functionalization

Figure 26. Electrochemical decarboxylation of glycine (A) Electrochemically mediated decarboxylation cross-coupling reaction of N-substituted glycines, (B) electrochemically mediated cyclization reaction and mechanism of N-arylglycine with quinoxalin-2(1H)-ones, and (C) electrochemically mediated three-component reaction of N-arylglycine, N-sulfonyl- ketimine and formaldehyde

Figure 27. Electrochemically mediated α-methoxylation of amino acids

Figure 28. Electrochemically mediated esterification reaction and mechanism of C-terminal carboxyl group of amino acids

Figure 29. Electrochemically mediated cross-coupling reaction and mechanism of amino acids with sulfides

Figure 30. (A) Electrochemically mediated peptide synthesis, (B) synthesis of leuprolide, and (C) proposed mechanism

References 74

[1]	Lau J. L.; Dunn M. K. Bioorg. Med. Chem. 2018, 26, 2700. doi: 10.1016/j.bmc.2017.06.052
[2]	(a) Craik D. J.; Fairlie D. P.; Liras S.; Price D. Chem. Biol. Drug Des. 2013, 81, 136. doi: 10.1111/cbdd.2012.81.issue-1 pmid: 33536635
	(b) Cooper B. M.; Iegre J.; O'Donovan D. H.; Halvarsson M. Ö.; Spring D. R. Chem. Soc. Rev. 2021, 50, 1480. doi: 10.1039/D0CS00556H pmid: 33536635
	(c) Muttenthaler M.; King G. F.; Adams D. J.; Alewood P. F. Nat. Rev. Drug Discov. 2021, 20, 309. doi: 10.1038/s41573-020-00135-8 pmid: 33536635
	(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. doi: 10.1002/anie.v56.3 pmid: 33536635
[3]	Fosgerau K.; Hoffmann T. Drug Discovery Today 2015, 20, 122. doi: 10.1016/j.drudis.2014.10.003 pmid: 25450771
[4]	(a) Ball Z. T. Acc. Chem. Res. 2013, 46, 560. doi: 10.1021/ar300261h pmid: 31318534
	(b) Yi L.; Sun H.; Wu Y. W.; Triola G.; Waldmann H.; Goody R. S. Angew. Chem., Int. Ed. 2010, 122, 9607. doi: 10.1002/ange.v122.49 pmid: 31318534
	(c) deGruyter J. N.; Malins L. R.; Baran P. S. Biochemistry 2017, 56, 3863. doi: 10.1021/acs.biochem.7b00536 pmid: 31318534
	(d) Cravatt B. F.; Wright A. T.; Kozarich J. W. Annu. Rev. Biochem. 2008, 77, 383. doi: 10.1146/biochem.2008.77.issue-1 pmid: 31318534
	(e) Luther A.; Bisang C.; Obrecht D. Bioorg. Med. Chem. 2018, 26, 2850. doi: 10.1016/j.bmc.2017.08.006 pmid: 31318534
	(f) Bai Z.; Wang H. Synlett 2020, 31, 199. doi: 10.1055/s-0039-1691495 pmid: 31318534
	(g) Brimble M. A.; Zhang S.;Rodriguez, L. M. M. D. L.; Li, F. F. Chem. Sci. 2023, 14, 7782. doi: 10.1039/D3SC02543H pmid: 31318534
	(h) Budisa N.; Völler J.; Koksch B.; Acevedo-Rocha C.; Kubyshkin V.; Agostini F. Angew. Chem., Int. Ed. 2017, 56, 9680. doi: 10.1002/anie.v56.33 pmid: 31318534
	(i) Chow H. Y.; Zhang Y.; Matheson E.; Li X. Chem. Rev. 2019, 119, 9971. doi: 10.1021/acs.chemrev.8b00657 pmid: 31318534
	(j) King T. A.; Kandemir J. M.; Walsh S. J.; Spring D. R. Chem. Soc. Rev. 2021, 50, 39. doi: 10.1039/D0CS00344A pmid: 31318534
	(k) Liu J.; Wang P.; Yan Z.; Yan J.; Kenry; Zhu Q. ChemBioChem 2021, 22, 2762. doi: 10.1002/cbic.v22.18 pmid: 31318534
	(l) Mondal S.; Chowdhury S. Adv. Synth. Catal. 2018, 360, 1884. doi: 10.1002/adsc.v360.10 pmid: 31318534
[5]	Bottecchia C.; Noël T. Chem.-Eur. J. 2018, 25, 26. doi: 10.1002/chem.v25.1
[6]	Noisier A. F.; Brimble M. A. Chem. Rev. 2014, 114, 8775. doi: 10.1021/cr500200x pmid: 25144592
[7]	Wang W.; Lorion M. M.; Shah J.; Kapdi A. R.; Ackermann L. Angew. Chem., Int. Ed. 2018, 57, 14700. doi: 10.1002/anie.v57.45
[8]	Tong H.-R.; Li B.; Li G.; He G.; Chen G. CCS Chem. 2021, 3, 1797. doi: 10.31635/ccschem.020.202000426
[9]	Meyer T. H.; Choi I.; Tian C.; Ackermann L. Chem 2020, 6, 2484. doi: 10.1016/j.chempr.2020.08.025
[10]	Siu J. C.; Fu N.; Lin S. Acc. Chem. Res. 2020, 53, 547. doi: 10.1021/acs.accounts.9b00529
[11]	Yamamoto K.; Kuriyama M.; Onomura O. Acc. Chem. Res. 2019, 53, 105. doi: 10.1021/acs.accounts.9b00513
[12]	Ang N. W.; Oliveira J. C.; Ackermann L. Angew. Chem., Int. Ed. 2020, 59, 12842. doi: 10.1002/anie.v59.31
[13]	Rosen B.; Werner E. J. Am. Chem. Soc. 2014, 136, 5571. doi: 10.1021/ja5013323
[14]	Mackay A. S.; Payne R. J.; Malins L. R. J. Am. Chem. Soc. 2021, 144, 23. doi: 10.1021/jacs.1c11185 pmid: 34968405
[15]	Brabec V.; Mornstein V. Biophys. Chem. 1980, 12, 159. pmid: 17000148
[16]	(a) Brunelle P.; Rauk A. J. Phys. Chem. 2004, 108, 11032. doi: 10.1021/jp046626j pmid: 4865316
	(b) Harriman A. J. Phys. Chem. 1987, 91, 6102. doi: 10.1021/j100308a011 pmid: 4865316
	(c) Jocelyn P. Eur. J. Biochem. 1967, 2, 327. pmid: 4865316
	(d) Navaratnam S.; Parsons B. J. Chem. Soc., Faraday Trans. 1998, 94, 2577. pmid: 4865316
	(e) Wilson G. S.; Glass R. S. J. Inorg. Biochem. 1994, 55, 87. doi: 10.1016/0162-0134(94)85031-3 pmid: 4865316
[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. doi: 10.1021/jacs.8b09372 pmid: 30422648
[18]	Ban H.; Gavrilyuk J.; Barbas III C. F. J. Am. Chem. Soc. 2010, 132, 1523. doi: 10.1021/ja909062q
[19]	Ban H.; Nagano M.; Gavrilyuk J.; Hakamata W.; Inokuma T.; Barbas III C. F. Bioconjugate Chem. 2013, 24, 520. doi: 10.1021/bc300665t
[20]	Jessica F.; Corentin W.; Sylvestre D.; Christian L.; André L. RSC Adv. 2013, 3, 24936. doi: 10.1039/c3ra44666b
[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. doi: 10.1021/bc500438h
	(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. doi: 10.1039/c3sc51694f
[22]	Bauer D. M.; Ahmed I.; Vigovskaya A.; Fruk L. Bioconjugate Chem. 2013, 24, 1094. doi: 10.1021/bc4001799
[23]	Madl C. M.; Heilshorn S. C. Bioconjugate Chem. 2017, 28, 724. doi: 10.1021/acs.bioconjchem.6b00720
[24]	Cui L.; Ma Y.; Li M.; Wei Z.; Huan Y.; Li H.; Fei Q.; Zheng L. Anal. Chem. 2021, 93, 4434. doi: 10.1021/acs.analchem.0c04337
[25]	Sato, S.; Matsumura, M.; Kadonosono, T.; Abe, S.; Ueno, T.; Ueda, H.; Nakamura, H. Bioconjugate Chem. 2020, 31, 1417. doi: 10.1021/acs.bioconjchem.0c00120
[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. doi: 10.1039/D1SC04809K
[27]	Song C.; Liu K.; Wang Z.; Ding B.; Wang S.; Weng Y.; Chiang C.-W.; Lei A. Chem. Sci. 2019, 10, 7982. doi: 10.1039/C9SC02218J
[28]	Stangier M.; Messinis A. M.; Oliveira J. C. A.; Yu H.; Ackermann L. Nat. Commun. 2021, 12, 4736. doi: 10.1038/s41467-021-25005-8
[29]	Hou X.; Kaplaneris N.; Yuan B.; Frey J.; Ohyama T.; Messinis A. M.; Ackermann L. Chem. Sci. 2022, 13, 3461. doi: 10.1039/D1SC07267F
[30]	You S.; Wang R.; Ma C.; Lu C.; Yang G.; Liu L.; Weng Y.; Gao M. Org. Chem. Front. 2023, 10, 4606. doi: 10.1039/D3QO00983A
[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. doi: 10.1021/jacs.6b06692
[33]	Wu J.; Abou-Hamdan H.; Guillot R.; Kouklovsky C.; Vincent G. Chem. Commun. 2020, 56, 1713. doi: 10.1039/C9CC09276E
[34]	Weng Y.; Xu X.; Chen H.; Zhang Y.; Zhuo X. Angew. Chem., Int. Ed. 2022, 61, e202206308. doi: 10.1002/anie.v61.41
[35]	Qiu Y.; Scheremetjew A.; Finger L. H.; Ackermann L. Chem.- Eur. J. 2020, 26, 3241. doi: 10.1002/chem.v26.15
[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. doi: 10.1002/ajoc.v12.1
[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. doi: 10.1021/jacs.9b01886 pmid: 30905151
[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. doi: 10.1021/acs.orglett.1c03500
[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. doi: 10.1021/jacs.1c09412 pmid: 35015533
[40]	Lamb C. M. G.; Shi J.; Wilden J. D.; Macmillan D. Org. Biomol. Chem. 2022, 20, 7343. doi: 10.1039/D2OB01499H
[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. doi: 10.1039/D1SC06757E
[43]	Liu L.; Xu Z.; Liu T.; Xu C.; Zhang W.; Hua X.; Ling F.; Zhong W. J. Org. Chem. 2022, 87, 11379. doi: 10.1021/acs.joc.2c00856
[44]	Wang R.; Wang J.; Zhang Y.; Wang B.; Xia Y.; Xue F.; Jin W.; Liu C. Adv. Synth. Catal. 2023, 365, 900. doi: 10.1002/adsc.v365.6
[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. doi: 10.1021/jacs.1c06572 pmid: 34596395
[46]	Zeng S.; Fang S.; Cai H.; Wang D.; Liu W.; Hu X.; Sun P.; Ruan Z. Chem. Asian J. 2022, 17, e202200762. doi: 10.1002/asia.v17.20
[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. doi: 10.1002/anie.v61.6
[49]	Li P.; Guo C.; Wang S.; Ma D.; Feng T.; Wang Y.; Qiu Y. Nat. Commun. 2022, 13, 3774. doi: 10.1038/s41467-022-31435-9
[50]	Wang Y.; Tang S.; Yang G.; Wang S.; Ma D.; Qiu Y. Angew. Chem., Int. Ed. 2022, 61, e202207746. doi: 10.1002/anie.v61.38
[51]	Liang H.; Julaiti Y.; Zhao C.-G.; Xie J. Nat. Synth. 2023, 2, 338. doi: 10.1038/s44160-022-00219-w
[52]	Huang H.; Lambert T. H. Angew. Chem., Int. Ed. 2021, 60, 11163. doi: 10.1002/anie.v60.20
[53]	Huang H.; Lambert T. H. J. Am. Chem. Soc. 2021, 143, 7247. doi: 10.1021/jacs.1c01967 pmid: 33949852
[54]	Klocke E.; Matzeit A.; Gockeln M.; Schäfer H. J. Chem. Ber. 1993, 126, 1623. doi: 10.1002/cber.v126:7
[55]	Shao X.; Zheng Y.; Tian L.; Martín-Torres I.; Echavarren A. M.; Wang Y. Org. Lett. 2019, 21, 9262. doi: 10.1021/acs.orglett.9b03696
[56]	Chen X.; Luo X.; Peng X.; Guo J.; Zai J.; Wang P. Chem. Eur. J. 2020, 26, 3226. doi: 10.1002/chem.v26.15
[57]	Barton L. M.; Chen L.; Blackmond D. G.; Baran P. S. Proc. Natl. Acad. Sci. 2021, 118, e2109408118. doi: 10.1073/pnas.2109408118
[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. doi: 10.1002/anie.v56.1
[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. doi: 10.1002/ange.v129.3
[60]	Köckinger M.; Hanselmann P.; Roberge D. M.; Geotti-Bianchini P.; Kappe C. O.; Cantillo D. Green Chem. 2021, 23, 2382. doi: 10.1039/D1GC00201E
[61]	Renaud P.; Seebach D. Angew. Chem.,Int. Ed. Engl. 1986, 25, 843. doi: 10.1002/anie.v25:9
[62]	Lin Y.; Malins L. R. Chem. Sci. 2020, 11, 10752. doi: 10.1039/D0SC03701J
[63]	Lin Y.; Malins L. R. J. Am. Chem. Soc. 2021, 143, 11811. doi: 10.1021/jacs.1c05718
[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. doi: 10.1002/adsc.v364.14
[65]	Cui J.-F.; Zhong W.-Q.; Huang J.-M. J. Org. Chem. 2023, 88, 1147. doi: 10.1021/acs.joc.2c02654
[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. doi: 10.1039/D2GC04906F
[67]	Gausmann M.; Kreidt N.; Christmann M. Org. Lett. 2023, 25, 2228. doi: 10.1021/acs.orglett.3c00403
[68]	Li Y.; Wang H.; Zhang H.; Lei A. Chin. J. Chem. 2021, 39, 3023. doi: 10.1002/cjoc.v39.11
[69]	Li C.-J. Acc. Chem. Res. 2009, 42, 335. doi: 10.1021/ar800164n
[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. doi: 10.1021/jacs.1c00288
[71]	Palma A.; Cárdenas J.; Frontana-Uribe B. A. Green Chem. 2009, 11, 283. doi: 10.1039/B815745F
[72]	Nagahara S.; Okada Y.; Kitano Y.; Chiba K. Chem. Sci. 2021, 12, 12911. doi: 10.1039/d1sc03023j pmid: 34745521
[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. doi: 10.1039/C7GC01575E pmid: 34270883
	(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. doi: 10.1039/c9gc01050e pmid: 34270883
	(c) Knauer S.; Koch N.; Uth C.; Meusinger R.; Avrutina O.; Kolmar H. Angew. Chem., Int. Ed. 2020, 59, 12984. doi: 10.1002/anie.v59.31 pmid: 34270883
	(d) Pawlas J.; Rasmussen J. H. ChemSusChem. 2021, 14, 3231. doi: 10.1002/cssc.202101028 pmid: 34270883

电化学修饰氨基酸和多肽类化合物的研究进展