Synthesis 2019; 51(14): 2759-2791
DOI: 10.1055/s-0037-1611852
review
© Georg Thieme Verlag Stuttgart · New York

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

a  Department of Chemistry, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden   Email: karkas@kth.se
,
a  Department of Chemistry, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden   Email: karkas@kth.se
,
b  Department of Chemistry, New York University, New York, NY 10003, USA   Email: bm2623@nyu.edu
,
a  Department of Chemistry, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden   Email: karkas@kth.se
› Author Affiliations
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 (eFirst)

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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