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Title
Japanese:Peptide Cyclization by the Use of Acylammonium Species 
English:Peptide Cyclization by the Use of Acylammonium Species 
Author
Japanese: Otoka Shamoto, Keiji Komuro, Naoto Sugisawa, Ting-Ho Chen, Hiroyuki Nakamura, Shinichiro Fuse.  
English: Otoka Shamoto, Keiji Komuro, Naoto Sugisawa, Ting-Ho Chen, Hiroyuki Nakamura, Shinichiro Fuse.  
Language English 
Journal/Book name
Japanese:Angewandte Chemie International Edition 
English:Angewandte Chemie International Edition 
Volume, Number, Page Vol. 62    No. 27    pp. e202300647
Published date May 10, 2023 
Publisher
Japanese:John Wiley & Sons, Ltd 
English:John Wiley & Sons, Ltd 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL https://doi.org/10.1002/anie.202300647
 
DOI https://doi.org/10.1002/anie.202300647
Abstract Abstract Although cyclic peptides have become increasingly important as drugs, the most conventional peptide cyclization method using moderately active coupling agents suffers from a lot of waste and high cost as well as long reaction times and burdensome purification. Herein, we report an unconventional approach to peptide cyclization that uses acylammonium species generated from inexpensive and less wasteful Me2NBn and ClCO2i-Pr. Using this approach, we observed the desired rapid activation of the C-terminus of cyclization precursors by an acylammonium ion for rapid and epimerization/dimerization-free cyclization of synthetically challenging peptides, including a difficult cyclization involving N-methyl amide bond formation. The ease of purification, productivities, and reaction mass efficiencies of our approach were significantly superior to those in previous reports. We synthesized a previously reported versicotide D analogue, and our data indicated that its assigned stereostructure should be revised.

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