Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation

Author(s)

Lima, Rafaely N. ^[1] ; Delgado, Jose A. C. ^[1] ; Bernardi, Darlon I. ^[2] ; Berlinck, Roberto G. S. ^[2] ; Kaplaneris, Nikolaos ^[3] ; Ackermann, Lutz ^[3] ; Paixao, Marcio W. ^[1]

Affiliation

^[1] Fed Univ Sao Carlos UFSCar, Dept Chem, Ctr Excellence Res Sustainable Chem CERSusChem, Rodovia Washington Luis, Km 235, SP 310, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Sao Paulo, Inst Quim Sao Carlos, CP 780, BR-13560970 Sao Carlos, SP - Brazil

^[3] Georg August Univ Gottingen, Inst Organ & Biomol, Tammannstr 2, D-37077 Gottingen - Germany

• Document type: Journal article
• Source: CHEMICAL COMMUNICATIONS; v. 57, n. 47, p. 5758-5761, JUN 14 2021.
• Web of Science Citations: 0

Abstract

We report a selective, mild, and efficient C-H functionalization of tryptophan and tryptophan-containing peptides with activated alpha-bromo-carbonyl compounds under visible-light irradiation. The protocol efficiency is outlined by the wide substrate scope and excellent tolerance of sensitive functional groups present in the amino acid side chains. The method can be successfully extended to access pharmaco-peptide conjugate scaffolds. (AU)

• 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 - Applied Research Centers Program
• FAPESP's process: 18/14595-0 - Application of Photocatalysis in Modification and Asymmetric Functionalization of Peptides
• Grantee: Rafaely Nascimento Lima
• Support Opportunities: Scholarships in Brazil - Post-Doctoral