Single Electron Transfer-based Peptide/protein Bioconjugations Driven by Biocompatible Energy Input

Overview

Journal Commun Chem

Publisher Springer Nature

Specialty Chemistry

Date 2023 Jan 27

PMID 36703459

Authors

Yue Weng

Chunlan Song

Chien-Wei Chiang

Aiwen Lei

Affiliations

Soon will be listed here.

Abstract

Bioconjugation reactions play a central facilitating role in engendering modified peptides and proteins. Early progress in this area was inhibited by challenges such as the limited range of substrates and the relatively poor biocompatibility of bioconjugation reagents. However, the recent developments in visible-light induced photoredox catalysis and electrochemical catalysis reactions have permitted significant novel reactivities to be developed in the field of synthetic and bioconjugation chemistry. This perspective describes recent advances in the use of biocompatible energy input for the modification of peptides and proteins mainly, via the single electron transfer (SET) process, as well as key future developments in this area.

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References

Bottecchia C, Noel T . Photocatalytic Modification of Amino Acids, Peptides, and Proteins. Chemistry. 2018; 25(1):26-42. PMC: 6348373. DOI: 10.1002/chem.201803074. View

Lin S, Yang X, Jia S, Weeks A, Hornsby M, Lee P . Redox-based reagents for chemoselective methionine bioconjugation. Science. 2017; 355(6325):597-602. PMC: 5827972. DOI: 10.1126/science.aal3316. View

van den Brink F, Zhang T, Ma L, Bomer J, Odijk M, Olthuis W . Electrochemical Protein Cleavage in a Microfluidic Cell with Integrated Boron Doped Diamond Electrodes. Anal Chem. 2016; 88(18):9190-8. DOI: 10.1021/acs.analchem.6b02413. View

Chen X, Wu Y . Selective chemical labeling of proteins. Org Biomol Chem. 2016; 14(24):5417-39. DOI: 10.1039/c6ob00126b. View

Yu Y, Zhang L, Buevich A, Li G, Tang H, Vachal P . Chemoselective Peptide Modification via Photocatalytic Tryptophan β-Position Conjugation. J Am Chem Soc. 2018; 140(22):6797-6800. DOI: 10.1021/jacs.8b03973. View

McCarver S, Qiao J, Carpenter J, Borzilleri R, Poss M, Eastgate M . Decarboxylative Peptide Macrocyclization through Photoredox Catalysis. Angew Chem Int Ed Engl. 2016; 56(3):728-732. PMC: 5225041. DOI: 10.1002/anie.201608207. View

Spicer C, Davis B . Selective chemical protein modification. Nat Commun. 2014; 5:4740. DOI: 10.1038/ncomms5740. View

Skubi K, Blum T, Yoon T . Dual Catalysis Strategies in Photochemical Synthesis. Chem Rev. 2016; 116(17):10035-74. PMC: 5083252. DOI: 10.1021/acs.chemrev.6b00018. View

Ban H, Gavrilyuk J, Barbas 3rd C . Tyrosine bioconjugation through aqueous ene-type reactions: a click-like reaction for tyrosine. J Am Chem Soc. 2010; 132(5):1523-5. DOI: 10.1021/ja909062q. View

10.

Matos M, Oliveira B, Martinez-Saez N, Guerreiro A, Cal P, Bertoldo J . Chemo- and Regioselective Lysine Modification on Native Proteins. J Am Chem Soc. 2018; 140(11):4004-4017. PMC: 5880509. DOI: 10.1021/jacs.7b12874. View

11.

Deming T . Functional Modification of Thioether Groups in Peptides, Polypeptides, and Proteins. Bioconjug Chem. 2016; 28(3):691-700. DOI: 10.1021/acs.bioconjchem.6b00696. View

12.

Sletten E, Bertozzi C . Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl. 2009; 48(38):6974-98. PMC: 2864149. DOI: 10.1002/anie.200900942. View

13.

Kubota K, Dai P, Pentelute B, Buchwald S . Palladium Oxidative Addition Complexes for Peptide and Protein Cross-linking. J Am Chem Soc. 2018; 140(8):3128-3133. PMC: 5831526. DOI: 10.1021/jacs.8b00172. View

14.

Gilis D, Massar S, Cerf N, Rooman M . Optimality of the genetic code with respect to protein stability and amino-acid frequencies. Genome Biol. 2001; 2(11):RESEARCH0049. PMC: 60310. DOI: 10.1186/gb-2001-2-11-research0049. View

15.

Lee H, Boyer N, Deng Q, Kim H, Sawyer T, Sciammetta N . Photoredox Ni-catalyzed peptide C(sp)-O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization. Chem Sci. 2019; 10(19):5073-5078. PMC: 6524625. DOI: 10.1039/c9sc00694j. View

16.

Ren J, Tian K, Jia L, Han X, Zhao M . Rapid Covalent Immobilization of Proteins by Phenol-Based Photochemical Cross-Linking. Bioconjug Chem. 2016; 27(10):2266-2270. DOI: 10.1021/acs.bioconjchem.6b00413. View

17.

Yan M, Kawamata Y, Baran P . Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance. Chem Rev. 2017; 117(21):13230-13319. PMC: 5786875. DOI: 10.1021/acs.chemrev.7b00397. View

18.

Ichiishi N, Caldwell J, Lin M, Zhong W, Zhu X, Streckfuss E . Protecting group free radical C-H trifluoromethylation of peptides. Chem Sci. 2018; 9(17):4168-4175. PMC: 5941281. DOI: 10.1039/c8sc00368h. View

19.

Sato S, Matsumura M, Kadonosono T, Abe S, Ueno T, Ueda H . Site-Selective Protein Chemical Modification of Exposed Tyrosine Residues Using Tyrosine Click Reaction. Bioconjug Chem. 2020; 31(5):1417-1424. DOI: 10.1021/acs.bioconjchem.0c00120. View

20.

Stephanopoulos N, Francis M . Choosing an effective protein bioconjugation strategy. Nat Chem Biol. 2011; 7(12):876-84. DOI: 10.1038/nchembio.720. View