Affiliation:
1. Faculty of Science and Engineering Chuo University 1-13-27 Kasuga Bunkyo-ku Tokyo 112-8551 Japan
2. Graduate School of Pharmaceutical Sciences Tohoku University 6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan
Abstract
AbstractSite‐specific introduction of multiple components into peptides is greatly needed for the preparation of densely functionalized and structurally uniform peptides. In this regard, N‐terminal‐specific peptide modification is attractive, but it can be difficult due to the presence of highly nucleophilic lysine ϵ‐amine. In this work, we developed a method for the N‐terminal‐specific dual modification of peptides through a three‐component [3+2] cycloaddition with aldehydes and maleimides under mild copper catalysis. This approach enables exclusive functionalization at the glycine N‐terminus of iminopeptides, regardless of the presence of lysine ϵ‐amine, thus affording the cycloadducts in excellent yields. Tolerating a broad range of functional groups and molecules, the present method provides the opportunity to rapidly construct doubly functionalized peptides using readily accessible aldehyde and maleimide modules.
Funder
Kato Memorial Bioscience Foundation
Tokyo Biochemical Research Foundation
Takahashi Industrial and Economic Research Foundation
Uehara Memorial Foundation
NOVARTIS Foundation (Japan) for the Promotion of Science
Japan Society for the Promotion of Science
Cited by
4 articles.
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