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Synthesis 2019; 51(14): 2759-2791
DOI: 10.1055/s-0037-1611852
DOI: 10.1055/s-0037-1611852
review
Recent Advances in Photoredox Catalysis Enabled Functionalization of α-Amino Acids and Peptides: Concepts, Strategies and Mechanisms
The organizing committee of the 53rd Bürgenstock Conference and the Swiss Chemical Society are gratefully acknowledged for a JSP fellowship to M.D.K. Financial support from KTH Royal Institute of Technology to M.D.K. is gratefully acknowledged. The Wenner-Gren Foundation and the Stiftelsen Olle Engkvist Byggmästare are kindly acknowledged for postdoctoral fellowships to J.L. and A.S., respectively.Further Information
Publication History
Received: 23 January 2019
Accepted after revision: 14 May 2019
Publication Date:
04 June 2019 (online)
Dedicated to Professor Björn Åkermark on the occasion of his 85th 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
-
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For reviews on non-proteinogenic amino acid building blocks, see:
For reviews on peptidomimetics, see:
For reviews on synthesis and applications of macrocyclic peptides, see:
For selected reviews on site-selective modification of amino acids and peptides, see:
For recent reviews on the application of radical intermediates in complex molecule synthesis, see:
For selected recent reviews on visible light photoredox catalysis, see:
For reviews on the applications of visible light photoredox catalysis in the synthesis of pharmaceutically relevant compounds, see:
For reviews on the photophysical properties of photoredox catalysts, see:
For recent reviews on transition-metal-catalyzed cross-couplings, see:
For reviews on decarboxylative coupling reactions, see:
For reviews on visible-light-mediated decarboxylative functionalizations, see:
For pioneering studies on photosensitized decarboxylation of N-hydroxyphthalimide (NHPI) based esters, see:
For related reports on redox-neutral Minisci-type alkylation, see:
For discussions on persistent radicals, see:
For selected recent reviews on the synthetic applications of hypervalent iodine reagents, see:
For reviews on dual catalysis involving the merger of metal and photoredox catalysis, see:
For reviews on hydrogen atom transfer (HAT), see:
For reviews on light-mediated reactions involving hydrogen atom transfer (HAT), see:
For reports on the synthesis of macrocyclic peptides involving photochemical decarboxylation using UV photolysis, see:
For leading reviews on cysteine bioconjugations, see:
For reports on visible-light-induced desulfurization of thiol- and disulfide-containing amino acids and peptides, see:
For leading reviews on C–H functionalization, see:
For reports on functionalization of tyrosine residues, see: