ArticleNature communications2019
Late-stage peptide C-H alkylation for bioorthogonal C-H activation featuring solid phase peptide synthesis.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Peptide Thioester and Triazole Derivatives Through On-Resin Dual-Modification of Peptide Thiosulfonates.Angewandte Chemie (International ed. in English) · 2026Article
- Late-Stage Functionalization of Peptides on the Solid Phase.Angewandte Chemie (International ed. in English) · 2026Review
- Advances in electrochemical peptide synthesis and modification.Nature reviews. Chemistry · 2026Review
- Making Blank Faces Expressive: Chemical Approaches to the Modification of Chemically Inert Peptides.Journal of peptide science : an official publication of the European Peptide Society · 2026Review
- Expanding the fluorescence toolkit: molecular design, synthesis and biological application of unnatural amino acids.Chemical science · 2025Review
- Late-Stage Amination of Peptides on the Solid Phase.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Ideas Behind the Tryptophan-Mediated Petasis Reaction (TMPR) Concept for Peptide Stapling.ChemMedChem · 2024Review
- Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan.Organic letters · 2023Article
- Modular synthesis of clickable peptides via late-stage maleimidation on C(7)-H tryptophan.Nature communications · 2023Article
- Transition-Metal-Catalyzed C-H Bond Activation for the Formation of C-C Bonds in Complex Molecules.Chemical reviews · 2023Review
- Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C-H activation.Chemical science · 2023Article
- Enzymatic Late-Stage Halogenation of Peptides.Chembiochem : a European journal of chemical biology · 2023Article
- Selective Labeling of Peptides with o-Carboranes via Manganese(I)-Catalyzed C-H Activation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Rationales Design von Phe-BODIPY-Aminosäuren als fluorogene Bausteine für den peptidbasierten Nachweis vonAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Rational Design of Phe-BODIPY Amino Acids as Fluorogenic Building Blocks for Peptide-Based Detection of Urinary Tract Candida Infections.Angewandte Chemie (International ed. in English) · 2022Article
- Late-stage stitching enabled by manganese-catalyzed C─H activation: Peptide ligation and access to cyclopeptides.Science advances · 2021Article
- Sustainable manganese catalysis for late-stage C-H functionalization of bioactive structural motifs.Beilstein journal of organic chemistry · 2021Review
- Silanol: a bifunctional group for peptide synthesis and late-stage functionalization.Chemical science · 2020Article
- Fluorescent amino acids as versatile building blocks for chemical biology.Nature reviews. Chemistry · 2020Review
- Late-stage C(spChemical science · 2020Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Methods for the late-stage diversification of structurally complex peptides hold enormous potential for advances in drug discovery, agrochemistry and pharmaceutical industries. While C-H arylations emerged for peptide modifications, they are largely limited to highly reactive, expensive and/or toxic reagents, such as silver(I) salts, in superstoichiometric quantities. In sharp contrast, we herein establish the ruthenium(II)-catalyzed C-H alkylation on structurally complex peptides. The additive-free ruthenium(II)carboxylate C-H activation manifold is characterized by ample substrate scope, racemization-free conditions and the chemo-selective tolerance of otherwise reactive functional groups, such as electrophilic ketone, bromo, ester, amide and nitro substituents. Mechanistic studies by experiment and computation feature an acid-enabled C-H ruthenation, along with a notable protodemetalation step. The transformative peptide C-H activation regime sets the stage for peptide ligation in solution and proves viable in a bioorthogonal fashion for C-H alkylations on user-friendly supports by means of solid phase peptide syntheses.
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