Preparation and application of chiral compounds containing chalcogens

• Grant number: 08/55401-1
• Support Opportunities: Research Projects - Thematic Grants
• Duration: March 01, 2009 - May 31, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: João Valdir Comasseto
• Grantee: João Valdir Comasseto
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Pesquisadores principais: Alcindo Aparecido dos Santos
• Associated scholarship(s): 12/14429-6 - Immobilization of microorganisms: application in reduction reactions of organic compounds containing chalcogens, BP.PD; 11/00256-0 - Synthesis and Biological Evaluation of Selenium and Tellurium Compounds as Inhibitors of the 20S proteasome, BP.PD

Abstract

Organic compounds of selenium and tellurium have been known for over 160 years. However, their application in organic synthesis and demonstration of their importance in biology only occurred from the second half of the 20th century. Our group has dedicated to this theme for over 3 decades, having developed novel synthetic methodologies, especially those based on tellurium organic compounds, which have been used in bioactive compounds synthesis. Moreover, in recent years, we have demonstrated that tellurium organic compounds act as powerful proteases inhibitors. The main goals of this project are: (a) to continue exploring the properties of organic compounds of Se and Te to be used as chiral building blocks in organic synthesis; (b) to use the building blocks developed in chiral synthesis of bioactive molecules; (c) to use biocatalysis in the dessimetrization of organic compounds containing Tellurium; (d) to use chiral organic compounds containing Tellurium in determining enantiomeric excesses by 125Te NMR; (e) to develop new protease inhibitors agents based on Selenium and Tellurium compounds.Summary of some results and perspectives: Methods have been developed for the preparation of amino and hydroxy tellurides. These compounds were obtained in the enantiomericaly enriched form by enzymatic kinetic resolution. Te/metal exchange reactions (metal = Li, Cu, Zn, Mn) were performed, generating the corresponding organometallic compounds. In some cases, these organometallic compounds were applied in the enantioselective synthesis of bioactive compounds, as insect pheromones and antibiotics. Studies on the activity of Se and Te organic compounds as cysteine protease inhibitors were carried out. Several new protease inhibitors containing Selenium and Tellurium were identified. Based on the results obtained, rational syntheses of novel inhibitors are being planned, which will be developed over the next two years. The enantiodiferentiation of mixtures of enantiomers by 125Te NMR was performed. Helical chiral polymers containing Se and Te to be used in detection of biomolecules in physiological systems will be prepared and their 125Te and 77Se NMR spectral characteristics will be explored. (AU)

Scientific publications

(7)

(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)

ARAUJO, JOSE E.; LODEIRO, CARLOS; CAPELO, JOSE L.; RODRIGUEZ-GONZALEZ, BENITO; DOS SANTOS, ALCINDO A.; SANTOS, HUGO M.; FERNANDEZ-LODEIRO, JAVIER. Novel nanocomposites based on a strawberry-like gold- coated magnetite (Fe@Au) for protein separation in multiple myeloma serum samples. NANO RESEARCH, v. 8, n. 4, p. 1189-1198, APR 2015. (08/55401-1, 11/11613-8)

RAFAELA C. CARMONA; EDISON P. WENDLER; GEORGE H. SAKAE; JOÃO V. COMASSETO; ALCINDO A. DOS SANTOS. A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids. Journal of the Brazilian Chemical Society, v. 26, n. 1, p. 117-123, 2015-01-00. (08/55401-1, 11/03244-2, 11/11613-8)

REIS DE SA, LEANDRO FIGUEIRA; TOLEDO, FABIANO TRAVANCA; DE SOUSA, BRUNO ARTUR; GONCALVES, AUGUSTO CESAR; TESSIS, ANA CLAUDIA; WENDLER, EDISON P.; COMASSETO, JOAO V.; DOS SANTOS, ALCINDO A.; FERREIRA-PEREIRA, ANTONIO. Synthetic organotelluride compounds induce the reversal of Pdr5p mediated fluconazole resistance in Saccharomyces cerevisiae. BMC Microbiology, v. 14, JUL 26 2014. (08/55401-1, 12/17093-9, 11/11613-8, 11/03244-2)

CARMONA, RAFAELA C.; SCHEVCIW, EVELYN P.; PETRARCA DE ALBUQUERQUE, JOAO L.; WENDLER, EDISON P.; DOS SANTOS, ALCINDO A.. Joint use of microwave and glycerol-zinc (II) acetate catalytic system in the synthesis of 2-pyridyl-2-oxazolines. GREEN PROCESSING AND SYNTHESIS, v. 2, n. 1, SI, p. 35-42, FEB 2013. (08/55401-1, 12/17093-9, 11/11613-8, 11/03244-2)

DONATONI, MARIA C.; JUNIOR, GILMAR A. B.; DE OLIVEIRA, KLEBER T.; ANDO, ROMULO A.; BROCKSOM, TIMOTHY J.; DOS SANTOS, ALCINDO A.. Solvent-free Diels-Alder reactions catalyzed by FeCl3 on Aerosil((R)) silica. Tetrahedron, v. 70, n. 20, p. 3231-3238, MAY 20 2014. (08/55401-1, 12/17093-9, 13/06532-4, 11/13993-2, 11/11613-8, 11/03244-2)

TAKATA, LEANDRO M. S.; GONCALVES, AUGUSTO C.; ANDO, RMULO A.; DOS SANTOS, ALCINDO A.; CAMARGO, PEDRO H. C.. Functionalization of gold and silver nanoparticles with diphenyl dichalcogenides probed by surface enhanced Raman scattering. Journal of Raman Spectroscopy, v. 43, n. 6, p. 712-717, JUN 2012. (08/55401-1)

CARMONA, RAFAELA C.; WENDLER, EDISON P.; SAKAE, GEORGE H.; COMASSETO, JOAO V.; DOS SANTOS, ALCINDO A.. A(3)- Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids. Journal of the Brazilian Chemical Society, v. 26, n. 1, p. 117-123, JAN 2015. (11/03244-2, 08/55401-1, 11/11613-8)