Modular Synthesis of Tripeptide Analogs with an Aminobitriazole Skeleton Using Diynyl Benziodoxolone as a Trivalent Platform.
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.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Japão