ArticleSynlett : accounts and rapid communications in synthetic organic chemistry2017
Thieme Chemistry Journals Awardees - Where Are They Now? Improved Fmoc Deprotection Methods for the Synthesis of Thioamide-Containing Peptides and Proteins.
Article in Synlett : accounts and rapid communications in synthetic organic chemistry, 2017. 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.
- Dual-Mode Thio-MacMillan Organocatalysts: Stereoselective Diels-Alder Reactions or Sacrificial Self-Cyclization to N-Bridged Bicyclic Lactams.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Programmable Helicity and Macrocycle Symmetry in β-Peptides via Site-Selective Thioamide Substitution.Journal of the American Chemical Society · 2025Article
- Complementary Strategies for Installation of Thioimidates into Peptide Backbones.The Journal of organic chemistry · 2024Article
- Thioimidates provide general access to thioamide, amidine, and imidazolone peptide-bond isosteres.Methods in enzymology · 2024Article
- Side-chain thioamides as fluorescence quenching probes.Biopolymers · 2021Article
- Incorporating thioamides into proteins by native chemical ligation.Methods in enzymology · 2021Article
- Fluorescent Probes for Studying Thioamide Positional Effects on Proteolysis Reveal Insight into Resistance to Cysteine Proteases.Chembiochem : a European journal of chemical biology · 2019Article
- Biosynthesis and Chemical Applications of Thioamides.ACS chemical biology · 2019Review
- A Conditionally Fluorescent Peptide Reporter of Secondary Structure Modulation.Chembiochem : a European journal of chemical biology · 2019Article
- Dithioamide substitutions in proteins: effects on thermostability, peptide binding, and fluorescence quenching in calmodulin.Chemical communications (Cambridge, England) · 2018Article
- Thioamide Substitution Selectively Modulates Proteolysis and Receptor Activity of Therapeutic Peptide Hormones.Journal of the American Chemical Society · 2017Article
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Authors and funding
5 authors.
Funding
Abstract
Site-selective incorporation of thioamides into peptides and proteins provides a useful tool for a wide range of applications. Current incorporation methods suffer from low yields as well as epimerization. Here, we describe how the use of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) rather than piperidine in fluorenylmethyloxycarbonyl (Fmoc) deprotection reduces epimerization and increases yields of thioamide-containing peptides. Furthermore, we demonstrate that the use of DBU avoids byproduct formation when synthesizing peptides containing side-chain thioamides.
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Registered trials
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