Lee C,
Thomson BJ,
Sammis GM.
*
University of British Columbia, Vancouver, Canada
Rapid and Column-Free Syntheses of Acyl Fluorides and Peptides Using
ex situ Generated Thionyl Fluoride.
Chem. Sci. 2022;
13: 188-194
DOI:
10.1039/d1sc05316g
Key words
peptide synthesis - thionyl fluoride - amino acid activation - acyl fluorides - liquid-phase peptide synthesis
Significance
The development of new methods for the synthesis of peptides is highly desirable for the discovery of peptide drugs. The authors have developed a novel method for the generation of SOF2
ex situ, and its use in the activation of amino acids in a peptide-coupling strategy for peptide synthesis.
Comment
The peptide-coupling reaction using ex situ-generated SOF2 proceeded smoothly to afford the desired peptides in high yields and with excellent selectivities. Inexpensive and readily available chemicals were used in the synthesis of SOF2. The method was also applied in liquid-phase syntheses of tri-, tetra-, and decapeptides.
