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Application of biocatalysis in organic synthesis using whole cells of microorganisms

Abstract

Aim is to develop methodology for conducting reactions racemic deracemization ofsecondary alcohols in order to obtain alcohols with high enantiomeric purity using whole cells of microorganisms, especially strains of yeasts and fungi. Establish the structural coverage of alcohols that suit the requirements of the active site of enzymes contained in microorganisms, such as withdrawing groups or donors positioned near hydroxyl function, alkyl substituents, aromatics, esters, etc. Beyond the effect of spatial accumulation of substituents around the alcohol function. To study the mechanism of the process and compare with the operation in the literature, exploring variables such as substrate concentration, pH, temperature, aerobic or anaerobic environment, strains and conditioning prior to addition of substrate. Apply deracemization methodology for the synthesis of molecules relevant alcohols from an economic standpoint as pharmacological activity. Perform reactions that allow execution preparative scale.The aim is to screen microorganisms, especially strains of yeast and fungi with the potential to effect reduction of the double bond of allylic alcohols. To establish the structural requirement of the double C = C bonds such as unsaturated substituents in position and influence of stereochemistry (Z) or (E) the biocatalytic process. To determine the occurrence (or not) the oxidation of allyl alcohol over the course of the reaction, a tandem process involving oxidation of the alcohol followed by reduction of the C=C double and intermediate aldehyde, or vice versa. Optimize the conditions of the reaction medium to determine the most efficient process, as the etching time of the strains prior to the addition of substrates , presence or absence of oxygen, temperature, pH, substrate concentration, among other factors. An optimized approach to carry out the time scaling aimed at the completion of the reaction preparative scale. (AU)

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Scientific publications (4)
(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 PAULA, BRUNO R. S.; ZAMPIERI, DAVILA S.; NASARIO, FABIO D.; RODRIGUES, J. AUGUSTO R.; MORAN, PAULO J. S. Regioselectivity Control of Enone Reduction Mediated by Aqueous Baker's Yeast with Addition of Ionic Liquid [bmim(PF6)]. BIOCATALYSIS AND AGRICULTURAL BIOTECHNOLOGY, v. 12, p. 166-171, OCT 2017. Web of Science Citations: 1.
PAULA, BRUNO R. S.; ZAMPIERI, DAVILA; RODRIGUES, J. AUGUSTO R.; MORANA, PAULO J. S. Bioreduction of alpha-Acetoxymethyl Enones: Proposal for an S(N)2 ` Mechanism Catalyzed by Enereductase. ADVANCED SYNTHESIS & CATALYSIS, v. 358, n. 22, p. 3555-3571, NOV 17 2016. Web of Science Citations: 4.
NASARIO, FABIO D.; CAZETTA, TARCILA; MORAN, PAULO J. S.; RODRIGUES, J. AUGUSTO R. Deracemization of 1-phenylethanol via tandem biocatalytic oxidation and reduction. TETRAHEDRON-ASYMMETRY, v. 27, n. 9-10, p. 404-409, JUN 1 2016. Web of Science Citations: 7.
CAZETTA, TARCILA; MORAN, PAULO J. S.; RODRIGUES, J. AUGUSTO R. Highly enantioselective deracemization of 1-phenyl-1,2-ethanediol and its derivatives by stereoinversion using Candida albicans in a one-pot process. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, v. 109, p. 178-183, NOV 2014. Web of Science Citations: 7.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.
Filed patent(s) as a result of this research project

PROCESSO FERMENTATIVO E SISTEMA INTEGRADO PARA A PRODUÇÃO DE ÁCIDOS ORGANICOS PCT/BR2017/000149 - Universidade Estadual de Campinas (UNICAMP) . Lucidio Cristovão Fardelone; José Roberto Nunhez; Gustavo Paim Valença; José Augusto Rosário Rodrigues; Paulo José Samenho Moran; Taciani dos Santos Bella de Jesus - December 2017, 19