Synthesis of non-proteinogenic amino acids and modification of peptides using photocatalysis

• Grant number: 22/04597-0
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: November 01, 2022
• End date: August 31, 2026
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: Emanuele Ferrari Pissinati
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated scholarship(s): 23/12718-5 - Bromodifluoroacetic acid derivatives as linkers for the synthesis of hybrid biomolecules using photoredox catalysis, BE.EP.DR

Abstract

The development of sustainable methodologies for the synthesis of biologic relevant molecules is of great importance for both academia (especially in organic synthesis and medicinal chemistry) and pharmaceutical industry. Thus, the use of visible light in synthesis of new compounds and systems with high degree of structural complexity has allowed the design of new methodologies. A special emphasis can be given to the use of photocatalyzed reactions in synthesis of unnatural amino acids and in modification of macromolecules.For these reasons and the efforts of our research group in development of photocatalytic process, the objectives of this project are the production of unnatural amino acids, through functionalization of natural tryptophan amino acid, followed by modification of peptides via organocatalytic methodologies, allowing us to obtain more economical, efficient and environmentally favorable strategies. Furthermore, we aim to carry out photocatalytic modifications of 2H-azirines with the insertion of radicals to olefin in C3, in a way of Giese addition.The development of this project will have collaboration of international researchers, and BEPE-internship will be requested to enable the application of the methodology in complex systems. Thus, it is important to emphasize that the planned inclusion of unnatural amino acids in peptides and proteins can alter their structural characteristics and so improve their biological properties and stability, factors of great interest to the pharmaceutical industries.

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)

DE JESUS, IVA S.; VELEZ, JEIMY A. C.; PISSINATI, EMANUELE F.; CORREIA, JOSE TIAGO M.; RIVERA, DANIEL G.; PAIXAO, MARCIO W.. Recent Advances in Photoinduced Modification of Amino Acids, Peptides, and Proteins. CHEMICAL RECORD, v. 24, n. 3, p. 41-pg., 2024-01-26. (21/06099-5, 22/04597-0)

PUGNAL, LUCAS V. B. L.; VEGA, KIMBERLY B.; PISSINATI, EMANUELE F.; CORREIA, JOSE TIAGO M.; ZUKERMAN-SCHPECTOR, JULIO; MARTIN, RUBEN; PAIXAO, MARCIO W.. 1,2-Arylsulfonylation of Vinyl Ethers and Esters Enabled by Dual Ni Catalysis. CHEMCATCHEM, v. N/A, p. 6-pg., 2023-06-19. (21/06099-5, 19/01560-6, 20/09353-7, 22/04597-0, 17/10015-6, 21/01354-7)

PISSINATI, EMANUELE F.; BARRETO, LIVIA M. S.; OPATZ, TILL; PAIXAO, MAARCIO W.. Photocatalytic Synthesis of Difluorinated Glycoamino Acids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides. Journal of Organic Chemistry, v. 90, n. 10, p. 6-pg., 2025-03-04. (22/04597-0, 21/06099-5, 23/12718-5)