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Updated: Jun 18, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Modular Synthesis of Tripeptide Analogs with an Aminobitriazole Skeleton Using Diynyl Benziodoxolone as a Trivalent
Takashi Kano1, Ryusei Uozumi1, Toshifumi Maruyama2
1Laboratory of Pharmaceutical Synthetic Chemistry, Faculty of Pharmaceutical Science, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
Abstract:
A new synthesis method of tripeptide analogs with an aminobitriazole skeleton was proposed. The method involves assembling three amino acid-derived modules at the amino group site and onto a triisopropylsilyl diynyl benziodoxolone by copper-catalyzed electrophilic diynylation of amino acid-derived sulfonamides, chemoselective azide-alkyne cycloadditions with amino acid-derived azides, and deprotection. Various complex aminobitriazoles substituted with pyrene, nucleoside, and N-acetylglucosamine were also synthesized. The produced aminobitriazoles have three sp3 chiral centers and a C-N axial chirality.
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