Recent Advances in Photoredox Catalysis Enabled Functionalization of α-Amino Acids and Peptides: Concepts, Strategies and Mechanisms

Jian-Quan Liu; Andrey Shatskiy; Bryan S. Matsuura; Markus D. Kärkäs

doi:10.1055/s-0037-1611852

Synthesis, Table of Contents

Synthesis 2019; 51(14): 2759-2791
DOI: 10.1055/s-0037-1611852

review

Recent Advances in Photoredox Catalysis Enabled Functionalization of α-Amino Acids and Peptides: Concepts, Strategies and Mechanisms

Jian-Quan Liu

^aDepartment of Chemistry, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden Email: karkas@kth.se

,

Andrey Shatskiy

^aDepartment of Chemistry, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden Email: karkas@kth.se

,

Bryan S. Matsuura *

^bDepartment of Chemistry, New York University, New York, NY 10003, USA Email: bm2623@nyu.edu

,

Markus D. Kärkäs *

^aDepartment of Chemistry, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden Email: karkas@kth.se

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Björn Åkermark on the occasion of his 85^th birthday

Published as part of the Bürgenstock Special Section 2018 Future Stars in Organic Chemistry

Abstract

The selective modification of α-amino acids and peptides constitutes a pivotal arena for accessing new peptide-based materials and therapeutics. In recent years, visible light photoredox catalysis has appeared as a powerful platform for the activation of small molecules via single-electron transfer events, allowing previously inaccessible reaction pathways to be explored. This review outlines the recent advances, mechanistic underpinnings, and opportunities of applying photoredox catalysis to the expansion of the synthetic repertoire for the modification of specific amino acid residues.

1 Introduction

2 Visible-Light-Mediated Functionalization of α-Amino Acids

2.1 Decarboxylative Functionalization Involving Redox-Active Esters

2.2 Direct Decarboxylative Coupling Strategies

2.3 Hypervalent Iodine Reagents

2.4 Dual Photoredox and Transition-Metal Catalysis

2.5 Amination and Deamination Strategies

3 Photoinduced Peptide Diversification

3.1 Gese-Type Bioconjugation Methods

3.2 Peptide Macrocyclization through Photoredox Catalysis

3.3 Biomolecule Conjugation through Arylation

3.4 C–H Functionalization Manifolds

4 Conclusions and Outlook

Key words

amino acids - electron transfer - peptides - photoredox catalysis - radicals - visible light

Full Text

References

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156 Ohshiro Y, Nakajima E, Goto Y, Fuse S, Takahashi T, Doi T, Suga H. ChemBioChem 2011; 12: 1183
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160a Hoyle CE, Bowman CN. Angew. Chem. Int. Ed. 2010; 49: 1540
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161 Bottecchia C, Rubens M, Gunnoo SB, Hessel V, Madder A, Noël T. Angew. Chem. Int. Ed. 2017; 56: 12702

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162a Gao X.-F, Du J.-J, Liu Z, Guo J. Org. Lett. 2016; 18: 1166
162b Lee M, Neukirchen S, Cabrele C, Reiser O. J. Pept. Sci. 2017; 23: 556

163 For an example of visible-light-induced trifluoromethylation and perfluoroalkylation of cysteine residues, see: Bottecchia C, Wei X.-J, Kuijpers KP. L, Hessel V, Noël T. J. Org. Chem. 2016; 81: 7301
164 Vara BA, Li X, Berritt S, Walters CR, Petersson EJ, Molander GA. Chem. Sci. 2018; 9: 336
165 Cheng W.-M, Shang R, Fu Y. ACS Catal. 2017; 7: 907

For leading reviews on C–H functionalization, see:

166a Daugulis O, Roane J, Tran LD. Acc. Chem. Res. 2015; 48: 1053
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167 Le C, Liang Y, Evans RW, Li X, MacMillan DW. C. Nature 2017; 547: 79
168 Yu Y, Zhang L.-K, Buevich AV, Li G, Tang H, Vachal P, Colletti SL, Shi Z.-C. J. Am. Chem. Soc. 2018; 140: 6797
169 For visible-light mediated functionalization of peptides with indoles, see: Zhu S, Rueping M. Chem. Commun. 2012; 48: 11960

For reports on functionalization of tyrosine residues, see:

170a Kim K, Fancy DA, Carney D, Kodadek T. J. Am. Chem. Soc. 1999; 121: 11896
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171 Wang C, Guo M, Qi R, Shang Q, Liu Q, Wang S, Zhao L, Wang R, Xu Z. Angew. Chem. Int. Ed. 2018; 57: 15841
172 For a related report on functionalization of α-amino acid derivatives with concomitant hydrogen evolution, see: Gao X.-W, Meng Q.-Y, Li J.-X, Zhong J.-J, Lei T, Li X.-B, Tung C.-H, Wu L.-Z. ACS Catal. 2015; 5: 2391
173 Wang Y, Li G.-X, Yang G, He G, Chen G. Chem. Sci. 2016; 7: 2679
174 For a related report on late-stage C–H fluorination on unprotected peptides, see: Yuan Z, Nodwell MB, Yang H, Malik N, Merkens H, Bénard F, Martin RE, Schaffer P, Britton R. Angew. Chem. Int. Ed. 2018; 57: 12733
175 Cismesia MA, Yoon TP. Chem. Sci. 2015; 6: 5426
176 Kärkäs MD, Matsuura BS, Stephenson CR. J. Science 2015; 349: 1285
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178 Choi GJ, Zhu Q, Miller DC, Gu CJ, Knowles RR. Nature 2016; 539: 268
179 Chu JC. K, Rovis T. Nature 2016; 539: 272
180 Morcillo SP, Dauncey EM, Kim JH, Douglas JJ, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2018; 57: 12945
181 For decarboxylative azidation of cyclic amino acids, see: Marcote DC, Street-Jeakings R, Dauncey E, Douglas JJ, Ruffoni A, Leonori D. Org. Biomol. Chem. 2019; 17: 1839
182 Lee H, Boyer NC, Deng Q, Kim H.-Y, Sawyer TK, Sciammetta N. Chem. Sci. 2019; 10: 5073