ArticleNature protocols2012
Synthesis of N-methylated cyclic peptides.
Article in Nature protocols, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 46 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
46 citing papers in PubMed.
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- Backbone Alterations in Cyclic Peptides Influence Both Membrane Permeability and Biological Activity.Journal of medicinal chemistry · 2025Article
- A Deep-Learning Neural Network Potential Accelerated First-Principles Study on the Structural Changes Modulated by Methylation and Solvation in 27 Protonated Tripeptides.The journal of physical chemistry. A · 2025Article
- Structural basis of apoptosis induction by the mitochondrial voltage-dependent anion channel.Nature communications · 2025Article
- Bispecific DNA-Peptide Probes for Targeting Receptor Pairs on Live Cells.Angewandte Chemie (International ed. in English) · 2025Article
- Discovery of Cell-Permeable Macrocyclic Cyclin A/B RxL Inhibitors that Demonstrate Antitumor Activity.Journal of medicinal chemistry · 2025Article
- Time-Reduced N-Methylation: Exploring a Faster Synthesis Technique.The Journal of organic chemistry · 2025Article
- Switching Roles─Exploring Concentration-Dependent Agonistic versus Antagonistic Behavior of Integrin Ligands.Journal of medicinal chemistry · 2025Article
- α-N-Methyltransferase regiospecificity is mediated by proximal, redundant enzyme-substrate interactions.Protein science : a publication of the Protein Society · 2025Article
- Rapid Peptide Cyclization Inspired by the Modular Logic of Nonribosomal Peptide Synthetases.Journal of the American Chemical Society · 2024Article
- The antimicrobial fibupeptide lugdunin forms water-filled channel structures in lipid membranes.Nature communications · 2024Article
- Biocompatible strategies for peptide macrocyclisation.Chemical science · 2024Review
- Gaussian accelerated molecular dynamics simulations facilitate prediction of the permeability of cyclic peptides.PloS one · 2024Article
- Protocol for Facile Synthesis of Fmoc-N-Me-AA-OH Using 2-CTC Resin as Temporary and Reusable Protecting Group.Methods and protocols · 2023Article
- An amide to thioamide substitution improves the permeability and bioavailability of macrocyclic peptides.Nature communications · 2023Article
- Review on Extraction, Modification, and Synthesis of Natural Peptides and Their Beneficial Effects on Skin.Molecules (Basel, Switzerland) · 2023Review
- Targeting integrin αvβ6 with gallium-68 tris (hydroxypyridinone) based PET probes.Dalton transactions (Cambridge, England : 2003) · 2022Article
- Applying Promiscuous RiPP Enzymes to Peptide BackboneACS chemical biology · 2022Article
- Amide Bonds Meet Flow Chemistry: A Journey into Methodologies and Sustainable Evolution.ChemSusChem · 2022Review
- Complex peptide natural products: Biosynthetic principles, challenges and opportunities for pathway engineering.Synthetic and systems biotechnology · 2022Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
This protocol presents a detailed description of the synthesis of N-methylated cyclic peptides. N-methylation is a powerful technique to modulate the physicochemical properties of peptides by introducing one or more methyl groups into the peptidic amide bonds. Together with peptide cyclization, this procedure confers unprecedented pharmacokinetic properties to the peptides, including metabolic stability, membrane permeability and even oral bioavailability. Here we describe two simplified methods of N-methylation of linear peptides on solid supports, which can be performed in less than 2 h and are applicable to any amino acid. Finally, we also describe two methods of peptide cyclization, which can be used to obtain the N-methylated cyclic peptide and which are not limited to specific peptide sequences. With this protocol, multiply N-methylated cyclic peptides can be synthesized in as little as 4-5 d.
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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.