Otake Y,
Shibata Y,
Hayashi Y,
Kawauchi S,
Nakamura H,
Fuse S.
* Nagoya University, Japan
N-Methylated Peptide Synthesis via Acyl N-Methylimidazolium Cation Generation Accelerated by a Brønsted Acid.
Angew. Chem. Int. Ed. 2020;
DOI:
10.1002/anie.202002106
Key words
Brønsted acid catalysis - methylimidazole - peptide coupling - amidation
Significance
Peptide synthesis is a significant process in organic chemistry and medicinal chemistry due to the increasing application of peptide drugs. The authors have developed an efficient Brønsted acid-catalyzed amide-bond formation approach to the preparation of peptides via acyl N-methylimidazolium cations.
Comment
Various dipeptides were synthesized from common amino acids. The yields of the reactions were moderate to good, with broad functional-group tolerance. Moreover, severe racemization was avoided in the reaction.
