Peptide Synthesis with α,α-Difluoro-β-Lactams

One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams: A. Tarui, M. Ueo, M. Morikawa, M. Tsuta, S. Iwasaki, N. Morishita, Y. Karuo, K. Sato, K. Kawai, M. Omote
Synthesis 2020, 52, DOI: 10.1055/s-0040-1707238


Fluorinated amino acids and peptidomimetics have extremely interesting properties in the realm of medicinal and biological chemistry and are increasingly used to impart bespoke properties – such as increased metabolic resistance and optimized pharmacokinetics – to bioactive compounds and drug candidates. The group of Professor Masaaki Omote from Setsunan University (Osaka, Japan) have recently reported a new strategy for incorporating α,α-difluoro-β-amino acid units in peptide sequences using a very straightforward synthetic approach.


Professor Omote said: “We discovered the interesting behavior of α,α-difluoro-β-lactams, which undergo one-pot ring-opening peptide elongation reaction with the assistance of 3,3,3-trifluoroethanol as a powerful reaction accelerator. This approach would help chemists synthesize peptides containing the xenobiotic α,α-difluoro-β-amino acid moiety.”

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