Biorredução de acetofenona por microrganismos do estado da Bahia
Autor(a) principal: | |
---|---|
Data de Publicação: | 2009 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UEFS |
Texto Completo: | http://localhost:8080/tede/handle/tede/453 |
Resumo: | The biorreduction has great importance in the production of optically pure substances and is widely used for asymmetric synthesis. Bioconversions occur with high specificity and efficiency because they are catalyzed by enzymes, forming one of the isomers from a pro-chiral substrate. This work had as main objective to evaluate the potential reduction of micro-organisms (yeasts, bacteria and fungi) isolated in the state of Bahia using as carbonyl substrate the acetophenone, analyzing its conversion into alcohol and identifying the enantiomeric excess produced. Strains of Saccharomyces cerevisiae isolated from sugar cane brandy distilleries of Bahia state, rhizobacteria isolated from Arachis pintoi (forage peanut) in southern Bahia and endophytic fungi isolated Hevea brasiliensis. The products were analyzed by gas chromatography coupled to mass spectrometry to verify the conversion of the substrate in alcohol and enantiomeric excess was determined by gas chromatography with chiral stationary phase. Of the 28 microorganisms evaluated 18 acted as biocatalysts. Products of reduction of acetophenone were obtained with yields between 6 and 79% and enantiomeric excess from 41 to 100%. Fungi CDC026, CDC086 and MDF077 converted acetophenone into (R)-alcohol, with ee of 54, 56, and 84%, while the other strains that showed positive results for acetophenone yielded the (S)-alcohol. Whereas 64% of test organisms were able to act as catalysts in the enantioseletive reduction of acetophenone, it was observed that the microbial diversity of the state of Bahia is a source of new catalysts for the production of enantiomeric pure compounds. |
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Lucchese, Angélica Mariahttp://lattes.cnpq.br/584045281802431380514707534http://lattes.cnpq.br/0262539103530308Miranda, Joseneide Alves de2017-02-17T23:59:53Z2009-08-31MIRANDA, Joseneide Alves de. Biorredução de acetofenona por microrganismos do estado da Bahia. 2009. 64 f. Dissertação (Mestrado Acadêmico em Biotecnologia) - Universidade Estadual de Feira de Santana, Feira de Santana, 2009.http://localhost:8080/tede/handle/tede/453The biorreduction has great importance in the production of optically pure substances and is widely used for asymmetric synthesis. Bioconversions occur with high specificity and efficiency because they are catalyzed by enzymes, forming one of the isomers from a pro-chiral substrate. This work had as main objective to evaluate the potential reduction of micro-organisms (yeasts, bacteria and fungi) isolated in the state of Bahia using as carbonyl substrate the acetophenone, analyzing its conversion into alcohol and identifying the enantiomeric excess produced. Strains of Saccharomyces cerevisiae isolated from sugar cane brandy distilleries of Bahia state, rhizobacteria isolated from Arachis pintoi (forage peanut) in southern Bahia and endophytic fungi isolated Hevea brasiliensis. The products were analyzed by gas chromatography coupled to mass spectrometry to verify the conversion of the substrate in alcohol and enantiomeric excess was determined by gas chromatography with chiral stationary phase. Of the 28 microorganisms evaluated 18 acted as biocatalysts. Products of reduction of acetophenone were obtained with yields between 6 and 79% and enantiomeric excess from 41 to 100%. Fungi CDC026, CDC086 and MDF077 converted acetophenone into (R)-alcohol, with ee of 54, 56, and 84%, while the other strains that showed positive results for acetophenone yielded the (S)-alcohol. Whereas 64% of test organisms were able to act as catalysts in the enantioseletive reduction of acetophenone, it was observed that the microbial diversity of the state of Bahia is a source of new catalysts for the production of enantiomeric pure compounds.A Biorredução tem grande importância na produção de substâncias opticamente puras, sendo amplamente utilizada para sínteses assimétricas. As bioconversões ocorrem com alta especificidade e eficiência por serem catalisadas por enzimas, formando um dos isômeros a partir de um substrato pró-quiral. O presente trabalho teve como objetivo principal avaliar o potencial redutor dos microrganismos (leveduras, bactérias e fungos) isolados no território baiano frente ao substrato carbonílico acetofenona; verificando a conversão do substrato (acetofenona) em álcool quiral e identificando o excesso enantiomérico com que as reações biocatalíticas ocorreram. Foram utilizadas culturas de Saccharomyces cerevisiae isoladas em cachaçarias do estado da Bahia, rizobactérias isoladas no sul da Bahia e fungos endofíticos. Foi testada a ação desses microrganismos sobre o substrato acetofenona. Os produtos foram analisados por Cromatografia gasosa acoplada a espetrometria de massa, para verificar a conversão do substrato em álcool; o excesso enantiomérico foi obtido em cromatógrafo gasoso equipado com coluna quiral obtendo-se separação para os isômeros da acetofenona com um excesso enantiomérico de até 100%, para a cepa bacteriana I68. Os fungos CDC026 e CDC086 converteram a acetofenona em (R)-álcool, as demais cepas que apresentaram resultados positivos para aceofenona produziram o (S)-álcool em excesso. Conclui-se que em geral os microrganismos testados apresentaram boa capacidade de redução da acetofenona em experimentos de biotransformação, constituindo-se fontes de compostos enantiomericamente puros.Submitted by Carolina Neves (carolinapon@uefs.br) on 2017-02-17T23:59:52Z No. of bitstreams: 1 DissertaçãoJoseneideAlves.pdf: 3612959 bytes, checksum: a4ba8033510286e66a0d4453ad52d71d (MD5)Made available in DSpace on 2017-02-17T23:59:53Z (GMT). No. of bitstreams: 1 DissertaçãoJoseneideAlves.pdf: 3612959 bytes, checksum: a4ba8033510286e66a0d4453ad52d71d (MD5) Previous issue date: 2009-08-31application/pdfporUniversidade Estadual de Feira de SantanaMestrado Acadêmico em BiotecnologiaUEFSBrasilDEPARTAMENTO DE CIÊNCIAS BIOLÓGICASBiorreduçãoLevedurasBactériasFungos endofíticosExcesso enantioméricoBioreductionYeastsRhizobacteriasEndophytic fungiEnantiomeric excessQUIMICA::QUIMICA ORGANICABiorredução de acetofenona por microrganismos do estado da Bahiainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis-54735432730516527826006006005026123383450589282-8194069717282802154info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UEFSinstname:Universidade Estadual de Feira de Santana (UEFS)instacron:UEFSORIGINALDissertaçãoJoseneideAlves.pdfDissertaçãoJoseneideAlves.pdfapplication/pdf3612959http://tede2.uefs.br:8080/bitstream/tede/453/2/Disserta%C3%A7%C3%A3oJoseneideAlves.pdfa4ba8033510286e66a0d4453ad52d71dMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82089http://tede2.uefs.br:8080/bitstream/tede/453/1/license.txt7b5ba3d2445355f386edab96125d42b7MD51tede/4532017-02-17 22:07:21.266oai:tede2.uefs.br:8080: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Biblioteca Digital de Teses e Dissertaçõeshttp://tede2.uefs.br:8080/PUBhttp://tede2.uefs.br:8080/oai/requestbcuefs@uefs.br|| bcref@uefs.br||bcuefs@uefs.bropendoar:2017-02-18T01:07:21Biblioteca Digital de Teses e Dissertações da UEFS - Universidade Estadual de Feira de Santana (UEFS)false |
dc.title.por.fl_str_mv |
Biorredução de acetofenona por microrganismos do estado da Bahia |
title |
Biorredução de acetofenona por microrganismos do estado da Bahia |
spellingShingle |
Biorredução de acetofenona por microrganismos do estado da Bahia Miranda, Joseneide Alves de Biorredução Leveduras Bactérias Fungos endofíticos Excesso enantiomérico Bioreduction Yeasts Rhizobacterias Endophytic fungi Enantiomeric excess QUIMICA::QUIMICA ORGANICA |
title_short |
Biorredução de acetofenona por microrganismos do estado da Bahia |
title_full |
Biorredução de acetofenona por microrganismos do estado da Bahia |
title_fullStr |
Biorredução de acetofenona por microrganismos do estado da Bahia |
title_full_unstemmed |
Biorredução de acetofenona por microrganismos do estado da Bahia |
title_sort |
Biorredução de acetofenona por microrganismos do estado da Bahia |
author |
Miranda, Joseneide Alves de |
author_facet |
Miranda, Joseneide Alves de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Lucchese, Angélica Maria |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/5840452818024313 |
dc.contributor.authorID.fl_str_mv |
80514707534 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0262539103530308 |
dc.contributor.author.fl_str_mv |
Miranda, Joseneide Alves de |
contributor_str_mv |
Lucchese, Angélica Maria |
dc.subject.por.fl_str_mv |
Biorredução Leveduras Bactérias Fungos endofíticos Excesso enantiomérico |
topic |
Biorredução Leveduras Bactérias Fungos endofíticos Excesso enantiomérico Bioreduction Yeasts Rhizobacterias Endophytic fungi Enantiomeric excess QUIMICA::QUIMICA ORGANICA |
dc.subject.eng.fl_str_mv |
Bioreduction Yeasts Rhizobacterias Endophytic fungi Enantiomeric excess |
dc.subject.cnpq.fl_str_mv |
QUIMICA::QUIMICA ORGANICA |
description |
The biorreduction has great importance in the production of optically pure substances and is widely used for asymmetric synthesis. Bioconversions occur with high specificity and efficiency because they are catalyzed by enzymes, forming one of the isomers from a pro-chiral substrate. This work had as main objective to evaluate the potential reduction of micro-organisms (yeasts, bacteria and fungi) isolated in the state of Bahia using as carbonyl substrate the acetophenone, analyzing its conversion into alcohol and identifying the enantiomeric excess produced. Strains of Saccharomyces cerevisiae isolated from sugar cane brandy distilleries of Bahia state, rhizobacteria isolated from Arachis pintoi (forage peanut) in southern Bahia and endophytic fungi isolated Hevea brasiliensis. The products were analyzed by gas chromatography coupled to mass spectrometry to verify the conversion of the substrate in alcohol and enantiomeric excess was determined by gas chromatography with chiral stationary phase. Of the 28 microorganisms evaluated 18 acted as biocatalysts. Products of reduction of acetophenone were obtained with yields between 6 and 79% and enantiomeric excess from 41 to 100%. Fungi CDC026, CDC086 and MDF077 converted acetophenone into (R)-alcohol, with ee of 54, 56, and 84%, while the other strains that showed positive results for acetophenone yielded the (S)-alcohol. Whereas 64% of test organisms were able to act as catalysts in the enantioseletive reduction of acetophenone, it was observed that the microbial diversity of the state of Bahia is a source of new catalysts for the production of enantiomeric pure compounds. |
publishDate |
2009 |
dc.date.issued.fl_str_mv |
2009-08-31 |
dc.date.accessioned.fl_str_mv |
2017-02-17T23:59:53Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
MIRANDA, Joseneide Alves de. Biorredução de acetofenona por microrganismos do estado da Bahia. 2009. 64 f. Dissertação (Mestrado Acadêmico em Biotecnologia) - Universidade Estadual de Feira de Santana, Feira de Santana, 2009. |
dc.identifier.uri.fl_str_mv |
http://localhost:8080/tede/handle/tede/453 |
identifier_str_mv |
MIRANDA, Joseneide Alves de. Biorredução de acetofenona por microrganismos do estado da Bahia. 2009. 64 f. Dissertação (Mestrado Acadêmico em Biotecnologia) - Universidade Estadual de Feira de Santana, Feira de Santana, 2009. |
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http://localhost:8080/tede/handle/tede/453 |
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por |
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por |
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Universidade Estadual de Feira de Santana |
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Mestrado Acadêmico em Biotecnologia |
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UEFS |
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Brasil |
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DEPARTAMENTO DE CIÊNCIAS BIOLÓGICAS |
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Universidade Estadual de Feira de Santana |
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