One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide-peptoid conjugates

Author(s)

de la Torre, Alexander F. ^{[1, 2]} ; Ali, Akbar ^[3] ; Galetto, Fabio Z. ^[4] ; Braga, Antonio L. ^[4] ; Delgado, Jose A. C. ^[2] ; Paixao, Marcio W. ^[2]

Affiliation

^[1] Univ Concepcion, Fac Ciencias Quim, Dept Quim Organ, Edmundo Larenas 234 Interior Casilla 160-C, Concepcion - Chile

^[2] Fed Univ Sao Carlos UFSCar, Ctr Excellence Res Sustainable Chem CERSusChem, Dept Chem, Rodovia Washington Luis, Km 235 SP 310, BR-13565905 Sao Carlos, SP - Brazil

^[3] Univ Sargodha, Dept Chem, Sargodha 40100 - Pakistan

^[4] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC - Brazil

• Document type: Journal article
• Source: MOLECULAR DIVERSITY; v. 24, n. 1, p. 1-10, FEB 2020.
• Web of Science Citations: 1

Abstract

A combined organocatalytic and multicomponent synthetic approach was designed for the preparation of selenium-based peptoids and peptide-peptoid conjugates. This single-step synthetic protocol comprises the organocatalytic asymmetric insertion of phenylselenium in the aldehyde moiety followed by the Ugi four-component reaction which results in obtaining the desired compounds in good-to-moderate yields and with good-to-excellent levels of stereoselectivity. {[}GRAPHICS] . (AU)

• FAPESP's process: 15/17141-1 - Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.
• Grantee: Ricardo Samuel Schwab
• Support Opportunities: Regular Research Grants
• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program