Modular Synthesis of Tripeptide Analogs with An Aminobitriazole Skeleton Using Diynyl Benziodoxolone as a Trivalent Platform

27 March 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 cop-per-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 multiple centers and a C–N axial chirality.

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Experimental procedures, characterization data, and NMR spectra
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