ArticleNature2016
Oxidative diversification of amino acids and peptides by small-molecule iron catalysis.
Article in Nature, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 71 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
71 citing papers in PubMed, 270 citations in OpenAlex.
- Functionalization of Peptides via Radical Arylation.Chembiochem : a European journal of chemical biology · 2026Review
- An alkyl-swap platform for late-stage modification of secondary N-methylamines.Nature chemistry · 2026Article
- Selective Hydroxylation of Collagen Model Peptides by Metal Catalysis.Chemistry & biodiversity · 2026Article
- B(COrganic letters · 2026Article
- 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
- Chemical Tagging ofJournal of the American Chemical Society · 2025Article
- Oxoammonium-Catalyzed Oxidation ofJournal of the American Chemical Society · 2024Article
- Selective C-N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis.Journal of the American Chemical Society · 2024Article
- α,β-Desaturation and Formal β-C(spJournal of the American Chemical Society · 2024Article
- Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines.Nature communications · 2024Article
- Advances in organocatalyzed synthesis of organic compounds.RSC advances · 2024Review
- Ferroptosis: a potential target for the treatment of atherosclerosis.Acta biochimica et biophysica Sinica · 2024Review
- Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing.Acta pharmaceutica Sinica. B · 2024Review
- Copper catalyzed Shono-type oxidation of proline residues in peptide.Science advances · 2023Article
- Article
- Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C-H activation.Chemical science · 2023Article
- Photo- and Metal-Mediated Deconstructive Approaches to Cyclic Aliphatic Amine Diversification.Journal of the American Chemical Society · 2023Article
- Synthesis of Tetrasubstituted Nitroalkenes and Preliminary Studies of Their Enantioselective Organocatalytic Reduction.Molecules (Basel, Switzerland) · 2023Article
- Selective editing of a peptide skeletonChemical science · 2022Article
- Heteroarylation of unactivated C-H bonds suitable for late-stage functionalization.Chemical science · 2022Article
11 more citing papers are in PubMed but not listed here.
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
Secondary metabolites synthesized by non-ribosomal peptide synthetases display diverse and complex topologies and possess a range of biological activities. Much of this diversity derives from a synthetic strategy that entails pre- and post-assembly oxidation of both the chiral amino acid building blocks and the assembled peptide scaffolds. The vancomycin biosynthetic pathway is an excellent example of the range of oxidative transformations that can be performed by the iron-containing enzymes involved in its biosynthesis. However, because of the challenges associated with using such oxidative enzymes to carry out chemical transformations in vitro, chemical syntheses guided by these principles have not been fully realized in the laboratory. Here we report that two small-molecule iron catalysts are capable of facilitating the targeted C-H oxidative modification of amino acids and peptides with preservation of α-centre chirality. Oxidation of proline to 5-hydroxyproline furnishes a versatile intermediate that can be transformed to rigid arylated derivatives or flexible linear carboxylic acids, alcohols, olefins and amines in both monomer and peptide settings. The value of this C-H oxidation strategy is demonstrated in its capacity for generating diversity: four 'chiral pool' amino acids are transformed to twenty-one chiral unnatural amino acids representing seven distinct functional group arrays; late-stage C-H functionalizations of a single proline-containing tripeptide furnish eight tripeptides, each having different unnatural amino acids. Additionally, a macrocyclic peptide containing a proline turn element is transformed via late-stage C-H oxidation to one containing a linear unnatural amino acid.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.