Ugi and Passerini reactions enable the incorporation of Delta AA into N-alkylated peptides and depsipeptides

Author(s)

Concepcion, Odette ; Penaloza, Francisco J. ; Lopez, Jhon Jairo ; Cabrera-Barjas, Gustavo ; Jimenez, Claudio A. ; Paixao, Marcio W. ; de la Torre, Alexander F.

• Document type: Journal article
• Source: NEW JOURNAL OF CHEMISTRY; v. 46, n. 24, p. 8-pg., 2022-05-12.

Abstract

This work renders operational simplicity under mild conditions to synthesize some N-alkylated peptides and depsipeptides containing olefins. A sequential one-pot protocol merging a multicomponent reaction with oxidative elimination of phenylselenoxide allows the formation of alpha,beta and beta,gamma olefin containing peptides and depsipeptides. Consequently, the regioselective construction of alpha,beta-dehydrobutyrine and alpha,beta-dehydro-homophenylalanine was possible using the Ugi four-component reaction; meanwhile, the Passerini three-component reaction produces the beta-enamide preferably. (AU)

• FAPESP's process: 21/06099-5 - Development of new photochemical methodologies for the synthesis of small molecule and biomolecule modifications
• Grantee: Márcio Weber Paixão
• Support Opportunities: Regular Research Grants