Development of New Photochemical Methodologies for the Synthesis of Complex Glycoconjugates

• Grant number: 23/05594-8
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: August 01, 2023
• End date: July 31, 2025
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: Lucas Loss Baldassari
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

This project aims to develop a methodology based on the use of fundamental principles of photochemistry in the synthesis of important compounds of the glycoconjugate class. For this, reactions between NHPI esters or Katritzky salts derived from carbohydrates (mono and polysaccharides) and dehydroalanines (from peptides) promoted by visible light will be studied. In this proposal, the following stand out: * Synthesis of glycoconjugates, compounds with high structural complexity and biological appeal;* Use of the potential of photoinduced reactions in visible light to carry out chemical transformations;* Use of complex substrates, such as polysaccharides and functionalized dehydroalanines with up to 20 amino acid units;* Control in the formation of stereocenters through the use of chiral acids;* Asymmetric formation of fluorinated glycoconjugates;* Development of carbohydrate chemistry, currently poorly explored by organic synthesis groups in Brazil;

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)

TORDATO, EVERTON A.; GONCALVES, RENAN O.; BALDASSARI, LUCAS L.; JIMENEZ, CLAUDIO A.; LUDTKE, DIOGO S.; PAIXAO, MARCIO W.. Expanding the Chemical Space of Electrophilic β-Glycosyl β-Lactams through Photoinduced Diastereoselective Functionalization. ORGANIC LETTERS, v. 26, n. 26, p. 6-pg., 2024-06-20. (21/06099-5, 23/05594-8)