ArticleJournal of the American Chemical Society2013
Site-specific protein transamination using N-methylpyridinium-4-carboxaldehyde.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 45 papers.
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Who cites it
45 citing papers in PubMed.
- Site-specific labelling of native peptides and proteins: chemical and enzymatic strategies.Beilstein journal of organic chemistry · 2026Review
- Efficient Synthesis of Chemically Recyclable Polyamides via Substituent Effects-Enabled Mechanistic Pathway.Angewandte Chemie (International ed. in English) · 2025Article
- Triazolinedione Modification of Prenylated Peptides, Proteins, and DNA: Toward a Single-Site Multilabeling Approach for Biomolecules.ACS omega · 2025Article
- Bioinspired Synthesis of Allysine for Late-Stage Functionalization of Peptides.Angewandte Chemie (International ed. in English) · 2024Article
- A pyridinium-based strategy for lysine-selective protein modification and chemoproteomic profiling in live cells.Chemical science · 2024Article
- Introduction of Carbonyl Groups into Antibodies.Molecules (Basel, Switzerland) · 2023Review
- The Evolving Landscape of Antibody-Drug Conjugates: In Depth Analysis of Recent Research Progress.Bioconjugate chemistry · 2023Review
- Supramolecular multivalency effects enhance imine formation in aqueous medium allowing for dynamic modification of enzymatic activity.Chemical science · 2023Article
- Development and Recent Advances in Lysine and N-Terminal Bioconjugation for Peptides and Proteins.Molecules (Basel, Switzerland) · 2023Review
- Designing Bioorthogonal Reactions for Biomedical Applications.Research (Washington, D.C.) · 2023Review
- Chemical Conjugation to Less Targeted Proteinogenic Amino Acids.Chembiochem : a European journal of chemical biology · 2022Review
- All-in-one disulfide bridging enables the generation of antibody conjugates with modular cargo loading.Chemical science · 2022Article
- An overview of chemo- and site-selectivity aspects in the chemical conjugation of proteins.Royal Society open science · 2022Article
- Precision Modification of Native Antibodies.Bioconjugate chemistry · 2021Review
- Asymmetric biomimetic transamination of α-keto amides to peptides.Nature communications · 2021Article
- Selective N-Arylation of p-Aminophenylalanine in Unprotected Peptides with Organometallic Palladium Reagents.Angewandte Chemie (International ed. in English) · 2021Article
- Exploiting Protein N-Terminus for Site-Specific Bioconjugation.Molecules (Basel, Switzerland) · 2021Review
- Modification of N-terminal α-amine of proteins via biomimetic ortho-quinone-mediated oxidation.Nature communications · 2021Article
- Linchpins empower promiscuous electrophiles to enable site-selective modification of histidine and aspartic acid in proteins.Chemical science · 2021Article
- Recent Advances in Quenchbody, a Fluorescent Immunosensor.Sensors (Basel, Switzerland) · 2021Review
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Authors and funding
7 authors.
Funding
Abstract
The controlled attachment of synthetic groups to proteins is important for a number of fields, including therapeutics, where antibody-drug conjugates are an emerging area of biologic medicines. We have previously reported a site-specific protein modification method using a transamination reaction that chemoselectively oxidizes the N-terminal amine of a polypeptide chain to a ketone or an aldehyde group. The newly introduced carbonyl can be used for conjugation to a synthetic group in one location through the formation of an oxime or a hydrazone linkage. To expand the scope of this reaction, we have used a combinatorial peptide library screening platform as a method to explore new transamination reagents while simultaneously identifying their optimal N-terminal sequences. N-Methylpyridinium-4-carboxaldehyde benzenesulfonate salt (Rapoport's salt, RS) was identified as a highly effective transamination reagent when paired with glutamate-terminal peptides and proteins. This finding establishes RS as a transamination reagent that is particularly well suited for antibody modification. Using a known therapeutic antibody, herceptin, it was demonstrated that RS can be used to modify the heavy chains of the wild-type antibody or to modify both the heavy and the light chains after N-terminal sequence mutation to add additional glutamate residues.
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Registered trials
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