ArticleAngewandte Chemie (International ed. in English)2014
Efficient amide bond formation through a rapid and strong activation of carboxylic acids in a microflow reactor.
Article in Angewandte Chemie (International ed. in English), 2014. 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.
- Straightforward, scalable, solution-phase synthesis of peptide bonds in flow.Journal of flow chemistry · 2025Article
- Synthesis of Dolutegravir Exploiting Continuous Flow Chemistry.The Journal of organic chemistry · 2023Article
- Rapid and column-chromatography-free peptide chain elongationChemical science · 2023Article
- Verification of preparations of (1H-indol-3-yl)methyl electrophiles and development of their microflow rapid generation and substitution.Communications chemistry · 2023Article
- Chemical Wastes in the Peptide Synthesis Process and Ways to Reduce Them.Iranian journal of pharmaceutical research : IJPR · 2022Review
- Optimization of Automated Synthesis of Amide-Linked RNA.ACS omega · 2022Article
- Amide Bonds Meet Flow Chemistry: A Journey into Methodologies and Sustainable Evolution.ChemSusChem · 2022Review
- Synthesis, Characterization and Evaluation of Peptide Nanostructures for Biomedical Applications.Molecules (Basel, Switzerland) · 2021Review
- Article
- Greening the synthesis of peptide therapeutics: an industrial perspective.RSC advances · 2020Review
- Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation.Nature communications · 2016Article
- Micro-total envelope system with silicon nanowire separator for safe carcinogenic chemistry.Nature communications · 2016Article
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3 authors.
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Abstract
The development of highly efficient amide bond forming methods which are devoid of side reactions, including epimerization, is important, and such a method is described herein and is based on the concept of rapid and strong activation of carboxylic acids. Various carboxylic acids are rapidly (0.5 s) converted into highly active species, derived from the inexpensive and less-toxic solid triphosgene, and then rapidly (4.3 s) reacted with various amines to afford the desired peptides in high yields (74%-quant.) without significant epimerization (≤3%). Our process can be carried out at ambient temperature, and only CO2 and HCl salts of diisopropylethyl amine are generated. In the long history of peptide synthesis, a significant number of active coupling reagents have been abandoned because the highly active electrophilic species generated are usually susceptible to side reactions such as epimerization. The concept presented herein should renew interest in the use of these reagents.
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