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Modular Synthesis of Tripeptide Analogs with an Aminobitriazole Skeleton Using Diynyl Benziodoxolone as a Trivalent Platform.
Kano, Takashi; Uozumi, Ryusei; Maruyama, Toshifumi; Tada, Norihiro; Itoh, Akichika.
Afiliação
  • Kano T; Laboratory of Pharmaceutical Synthetic Chemistry, Faculty of Pharmaceutical Science, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
  • Uozumi R; Laboratory of Pharmaceutical Synthetic Chemistry, Faculty of Pharmaceutical Science, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
  • Maruyama T; Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.
  • Tada N; Laboratory of Pharmaceutical Synthetic Chemistry, Faculty of Pharmaceutical Science, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
  • Itoh A; Laboratory of Pharmaceutical Synthetic Chemistry, Faculty of Pharmaceutical Science, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
J Org Chem ; 89(16): 11761-11765, 2024 Aug 16.
Article em En | MEDLINE | ID: mdl-39082689
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.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Japão

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Japão