ArticleChembiochem : a European journal of chemical biology2011
A reversible protection strategy to improve Fmoc-SPPS of peptide thioesters by the N-Acylurea approach.
Article in Chembiochem : a European journal of chemical biology, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 68 citations in OpenAlex.
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- Review on the o-Aminoaniline Moiety in Peptide and Protein Chemistry.Chembiochem : a European journal of chemical biology · 2025Review
- Safety-Catch Linkers for Solid-Phase Peptide Synthesis.Molecules (Basel, Switzerland) · 2024Review
- Development of Convergent Hybrid Phase Ligation for Efficient and Convenient Total Synthesis of Proteins.Peptide science (Hoboken, N.J.) · 2023Article
- Total Chemical Synthesis of LC3A and LC3B Activity-Based Probes.Biomedicines · 2023Article
- A versatileChemical science · 2022Article
- Recent advances in the synthesis of C-terminally modified peptides.Organic & biomolecular chemistry · 2020Review
- Sequence Diversification by Divergent C-Terminal Elongation of Peptides.The Journal of organic chemistry · 2018Article
- Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and estersChemical science · 2018Article
- Exploiting the MeDbz Linker To Generate Protected or Unprotected C-Terminally Modified Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation.Chemical science · 2017Article
- Article
- Expanding the chemical toolbox for the synthesis of large and uniquely modified proteins.Nature chemistry · 2016Review
- Chemical Synthesis of Phosphorylated Histone H2A at Tyr57 Reveals Insight into the Inhibition Mode of the SAGA Deubiquitinating Module.Angewandte Chemie (International ed. in English) · 2016Article
- Hybrid phase ligation for efficient synthesis of histone proteins.Organic & biomolecular chemistry · 2016Article
- Linker histone H1 and H3K56 acetylation are antagonistic regulators of nucleosome dynamics.Nature communications · 2015Article
- Histone core phosphorylation regulates DNA accessibility.The Journal of biological chemistry · 2015Article
- Chemical and biological tools for the preparation of modified histone proteins.Topics in current chemistry · 2015Article
- Synthesis of thioester peptides for the incorporation of thioamides into proteins by native chemical ligation.Journal of peptide science : an official publication of the European Peptide Society · 2014Article
- Making Ends Meet: Microwave-Accelerated Synthesis of Cyclic and Disulfide Rich Proteins Via In Situ Thioesterification and Native Chemical Ligation.International journal of peptide research and therapeutics · 2013Article
Corrections and comments
- Erratum issued
Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
C-terminal peptide thioesters are an essential component of the native chemical ligation approach for the preparation of fully or semisynthetic proteins. However, the efficient generation of C-terminal thioesters by Fmoc solid-phase peptide synthesis remains a challenge. The recent N-acylurea approach to thioester synthesis relies on the deactivation of one amine of 3,4-diaminobenzoic acid (Dbz) during Fmoc SPPS. Here, we demonstrate that this approach results in the formation of side products through the over-acylation of Dbz, particularly when applied to Gly-rich sequences. We find that orthogonal allyloxycarbonyl (Alloc) protection of a single Dbz amine eliminates these side products. We introduce a protected Fmoc-Dbz(Alloc) base resin that may be directly used for synthesis with most C-terminal amino acids. Following synthesis, quantitative removal of the Alloc group allows conversion to the active N-acyl-benzimidazolinone (Nbz) species, which can be purified and converted in situ to thioester under ligation conditions. This method is compatible with the automated preparation of peptide-Nbz conjugates. We demonstrate that Dbz protection improves the synthetic purity of Gly-rich peptide sequences derived from histone H4, as well as a 44-residue peptide from histone H3.
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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.