ArticleBioconjugate chemistry2021
Traceless Click-Assisted Native Chemical Ligation Enabled by Protecting Dibenzocyclooctyne from Acid-Mediated Rearrangement with Copper(I).
Article in Bioconjugate chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 23 citations in OpenAlex.
- Toward Ideal Proximity-Driven Reactions in Chemical Biology.Chembiochem : a European journal of chemical biology · 2026Review
- Peptide Marriages: Modular Assembly of Multi-Agonist Therapeutics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Development of a Prostate-Specific Antigen Targeted Dual Drug Conjugate for Prostate Cancer Therapy.ACS omega · 2025Article
- Selective Activation of Peptide-Thioester Precursors for Templated Native Chemical Ligations.Angewandte Chemie (International ed. in English) · 2025Article
- Chemically Induced Dimerization via Nanobody Binding Facilitates in Situ Ligand Assembly and On-Demand GPCR Activation.JACS Au · 2024Article
- Chemical Synthesis of Human Proteoforms and Application in Biomedicine.ACS central science · 2024Review
- Azole reagents enabled ligation of peptide acyl pyrazoles for chemical protein synthesis.Chemical science · 2024Article
- Exploring the Chemical Properties and Medicinal Applications of Tetramethylthiocycloheptyne Sulfoximine Used in Strain-Promoted Azide-Alkyne Cycloaddition Reactions.Pharmaceuticals (Basel, Switzerland) · 2023Article
- Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization.Molecules (Basel, Switzerland) · 2023Article
- D-Peptide and D-Protein Technology: Recent Advances, Challenges, and Opportunities.Chembiochem : a European journal of chemical biology · 2023Review
- Discrete, Chiral Polymer-Insulin Conjugates.Journal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
4 authors at 3 institutions in 1 country.
Funding
Abstract
The scope of proteins accessible to total chemical synthesis via native chemical ligation (NCL) is often limited by slow ligation kinetics. Here we describe Click-Assisted NCL (CAN), in which peptides are incorporated with traceless "helping hand" lysine linkers that enable addition of dibenzocyclooctyne (DBCO) and azide handles. The resulting strain-promoted alkyne-azide cycloaddition (SPAAC) increases their effective concentration to greatly accelerate ligations. We demonstrate that copper(I) protects DBCO from acid-mediated rearrangement during acidic peptide cleavage, enabling direct production of DBCO synthetic peptides. Excitingly, triazole-linked model peptides ligated rapidly and accumulated little side product due to the fast reaction time. Using the
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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.