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Recent Advances in Photoredox Catalysis Enabled Functionalization of alpha-Amino Acids and Peptides: Concepts, Strategies and Mechanisms
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. KTH Royal Inst Technol, Dept Chem, S-10044 Stockholm, Sweden..
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
NYU, Dept Chem, New York, NY 10003 USA..
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.ORCID iD: 0000-0002-6089-5454
2019 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 51, no 14, p. 2759-2791Article, review/survey (Refereed) Published
Abstract [en]

The selective modification of alpha-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 alpha-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

Place, publisher, year, edition, pages
GEORG THIEME VERLAG KG , 2019. Vol. 51, no 14, p. 2759-2791
Keywords [en]
amino acids, electron transfer, peptides, photoredox catalysis, radicals, visible light
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-257577DOI: 10.1055/s-0037-1611852ISI: 000479153600002Scopus ID: 2-s2.0-85068226160OAI: oai:DiVA.org:kth-257577DiVA, id: diva2:1353063
Note

QC 20190920

Available from: 2019-09-20 Created: 2019-09-20 Last updated: 2019-09-20Bibliographically approved

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Shatskiy, AndreyKärkäs, Markus D.

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