ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Solid-Phase Peptide Modification via Deaminative Photochemical Csp
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Late-Stage Functionalization of Peptides on the Solid Phase.Angewandte Chemie (International ed. in English) · 2026Review
- Late-Stage Native Peptide Modification Approach to the Total Synthesis of Koshidacins A and B.JACS Au · 2025Article
- Late-Stage Serine Modification Enables Noncanonical Peptide Synthesis.Journal of the American Chemical Society · 2025Article
- Late-Stage Amination of Peptides on the Solid Phase.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Late-stage installation and functionalization of alkyl pyridiniums: a general HTE amenable strategy to access diverse aryl alanine containing macrocyclic peptides.Chemical science · 2025Article
- Peptide Boronic Acids by Late-Stage Hydroboration on the Solid Phase.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- On-Resin Photochemical Decarboxylative Arylation of Peptides.Organic letters · 2024Article
- Beyond 20 in the 21st Century: Prospects and Challenges of Non-canonical Amino Acids in Peptide Drug Discovery.ACS medicinal chemistry letters · 2023Review
- Diversifying Amino Acids and Peptides via Deaminative Reductive Cross-Couplings Leveraging High-Throughput Experimentation.Journal of the American Chemical Society · 2023Article
- Late-Stage Functionalisation of Peptides on the Solid Phase by an Iodination-Substitution Approach.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Solid-Phase Photochemical Peptide Homologation Cyclization.Organic letters · 2022Article
- Solid-Phase Peptide Modification via Deaminative Photochemical CspChemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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Authors and funding
5 authors.
Funding
Abstract
Introduction of unnatural amino acids can significantly improve the binding affinity and stability of peptides. Commercial availability of such amino acids is limited, and their synthesis is a long and tedious process. We here describe a method that allows the functionalization of peptides directly on solid-support by converting lysine residues to Katritzky salts, and subjecting them to a photochemical Giese reaction under mild reaction conditions. The method avoids the need for amino acid synthesis and instead offers a late-stage modification route for rapid peptide diversification. While numerous modification approaches at the lysine amine have been described, this work provides the first example of deaminative functionalization of peptides at lysine. The two-step protocol is compatible with various substrates, lysine analogues, resins, and all proteinogenic amino acids. Finally, by leveraging solid-phase modification, this protocol facilitates the functionalization of longer peptides as was demonstrated using biologically relevant peptides of up to 15 amino acids.
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