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BIGINELLI reaction (synthesis and chemoenzymatic resolution) and biotransformation of steroids by microorganisms

Grant number: 19/07654-2
Support type:Regular Research Grants
Duration: September 01, 2019 - August 31, 2021
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Andre Luiz Meleiro Porto
Grantee:Andre Luiz Meleiro Porto
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

Part I of this Regular Research Grant project will study a class of compounds called dihydropyrimidinones (DHPMs), which are known to have a variety of biological properties. Thus, synthetic methodologies will be developed with the purpose of obtaining numerous racemic DHPMs, most of them unpublished in the literature. These compounds will undergo biological assays concerning the negligible diseases caused by protozoa such as leishmaniasis and Chagas diseases. As well, the potential of these compounds will be evaluated against tumor cells and immunomodulatory properties. Also racemic DHPMs containing the tetrazole nucleus will be synthesized, which is known to have relevant biological properties. The racemic DHPMs will be submitted to the enzymatic kinetic resolution, which will be performed after a screening process involving the use of commercial enzymes, in order to perform the separation of the enantiomers. The enantiomerically pure compounds will be evaluated in the same biological assays. In Part II the biotransformation reactions of steroids by marine environment fungi will be investigated, mainly in electrons not activated electrons. Isolation and identification of the main biotransformation products of the 17±-ethynylestradiol steroids, nandrolone decanoate, among others, will be performed and analytical techniques (LC-UV, LC-MS, GC-MS, NMR) will be used. The contribution of this project is important for the areas of organic chemistry, biocatalysis, pharmaceutical, environmental, as well as for the training of qualified human resources in the area of biotechnology, through the use of biological agents for the production of bioactive compounds. (AU)