ArticleAngewandte Chemie (International ed. in English)2021
Enabling Cysteine-Free Native Chemical Ligation at Challenging Junctions with a Ligation Auxiliary Capable of Base Catalysis.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 32 citations in OpenAlex.
- Chemical Ligation of Backbone N-hydroxylated Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Impact of Glycoclustering on Stiffening of MUC5AC Peptides Revealed by High-Efficiency Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Chemical Synthesis of Human Proteoforms and Application in Biomedicine.ACS central science · 2024Review
- Spontaneous Peptide Ligation Mediated by Cysteamine.JACS Au · 2024Article
- Enzymatic Fluoromethylation as a Tool for ATP-Independent Ligation.Angewandte Chemie (International ed. in English) · 2024Article
- Enzymatic Fluoromethylation as a Tool for ATP-Independent Ligation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2024Article
- Light-Cleavable Auxiliary for Diselenide-Selenoester Ligations of Peptides and Proteins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Chemical tools for study and modulation of biomolecular phase transitions.Chemical science · 2022Review
- Enhancing Auxiliary-Mediated Native Chemical Ligation at Challenging Junctions with Pyridine Scaffolds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- A versatileChemical science · 2022Article
- Synthesis of the l- and d-SH2 domain of the leukaemia oncogene Bcr-Abl.RSC chemical biology · 2022Article
- Enabling Cysteine-Free Native Chemical Ligation at Challenging Junctions with a Ligation Auxiliary Capable of Base Catalysis.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Ligation auxiliaries are used in chemical protein synthesis to extend the scope of native chemical ligation (NCL) beyond cysteine. However, auxiliary-mediated ligations at sterically demanding junctions have been difficult. Often the thioester intermediate formed in the thiol exchange step of NCL accumulates because the subsequent S→N acyl transfer is extremely slow. Here we introduce the 2-mercapto-2-(pyridin-2-yl)ethyl (MPyE) group as the first auxiliary designed to aid the ligation reaction by catalysis. Notably, the MPyE auxiliary provides useful rates even for junctions containing proline or a β-branched amino acid. Quantum chemical calculations suggest that the pyridine nitrogen acts as an intramolecular base in a rate-determining proton transfer step. The auxiliary is prepared in two steps and conveniently introduced by reductive alkylation. Auxiliary cleavage is induced upon treatment with TCEP/morpholine in presence of a Mn
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