Application of Photocatalysis in Modification and Asymmetric Functionalization of Peptides

• Grant number: 18/14595-0
• Support Opportunities: Scholarships in Brazil - Post-Doctorate
• Effective date (Start): March 01, 2019
• Effective date (End): February 28, 2022
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: Rafaely Nascimento Lima
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

In the last decades, the emphasis on applying the principles of Green Chemistry has been boosting the chemical industry and academia to change their behavior towards the application of a more sustainable chemistry. Having as a common goal, obtaining the desired product in as few steps as possible, high yield and the use of non-toxic reagents. In this context, the growing recognition of the environmental benefits presented by photochemical reactions realized in the visible light wavelengths spectrum, compared to conventional thermal methods, has stimulated the scientific community in search efficient photochemical methodologies, with simple operation and efficiency, aiming the development of new synthetic strategies to obtain biologically relevant organic compounds. Therefore, this research project proposes the exploration of synthetic methodologies via photochemistry provided by visible light, using photoredox catalysis processes mediated by transition metal complexes, photo-organocatalysts, photosensitizers and the formation of EDA complexes. In the first stage, synthetic procedures applied to photocatalysis will be developed for the modification of peptides through the functionalization of tryptophan residues, and we also intend to carry out asymmetric modifications in peptides using glycine as the aminoacid target, which is still not found at literature. All peptides obtained will undergo biological and conformational tests to analyze the effects caused by changes in their biological activities and stabilities. It is important highlight that aminoacids functionalization in peptides and assymmetric modifications of peptides using photocatalysis are innovative approaches worldwide especially in Brazil, representing an excellent opportunity to obtain compounds of high biological interest based in a sustainable perspective and Green Chemistry protocol.

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

LIMA, RAFAELY N.; DELGADO, JOSE A. C.; BERNARDI, DARLON I.; BERLINCK, ROBERTO G. S.; KAPLANERIS, NIKOLAOS; ACKERMANN, LUTZ; PAIXAO, MARCIO W.. Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation. CHEMICAL COMMUNICATIONS, v. 57, n. 47, p. 5758-5761, JUN 14 2021. (14/50249-8, 18/14595-0)

WANG, WEI; WU, JUN; KUNIYIL, ROSITHA; KOPP, ADELINA; LIMA, RAFAELY NASCIMENTO; ACKERMANN, LUTZ. Peptide Late-Stage Diversifications by Rhodium-Catalyzed Tryptophan C7 Amidation. CHEM, v. 6, n. 12, p. 3428-3439, DEC 3 2020. (18/14595-0)