Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFC |
Texto Completo: | http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=8904 |
Resumo: | Herein we describe the study biocatalytic potential of the whole cell of microorganisms isolated from a plant belonging to Cactacea family, Nopalea cochenillifera (L.) Salm- Dyck, popularly known as âpalma doceâ or âpalma forrageiraâ. The microorganisms were isolated by induction technique using as acetophenone susbtrate. Among the microorganisms strains (I-1, I-2, I-3, I-4) only I-2, (Pseudomonas sp), was effective as biocatalyst in reducing the acetophenone. The best conditions for carrying out the bioreduction of acetophenone were as follows: 1g of resting cells of Pseudomonas sp, resuspended in buffer solution pH 7, at 28 Â C and rotation of 175 r.p.m for 4 days, obtaining the (S)-1-phenylethanol with conversion of 77% e.e. and 89%. The bioreduction study, using the Pseudomonas sp strain, was extended to the following derivatives of acetophenone, 4-methoxy-acetophenone (2a), 4-methyl acetophenone (3a), 4-nitro-acetophenone (4a), 4 -bromo-acetophenone (5a), 4-chloro-acetophenone (6a), 4-fluoro-acetophenone (7a), 3-methoxy-acetophenone (8a), 3-methyl acetophenone (9a), 3-nitro-acetophenone (10a) 2-methoxy-acetophenone (11a), 2-methyl acetophenone (12a), 2-nitro-acetophenone (13a), 2-bromo-acetophenone (14a), 2-chloro-acetophenone (15a), 2 - fluoro-acetophenone (16a). It is not worthy that all the alcohols were obtained with Prelog selectivity (S configuration). In general, the best results were obtained for the derivatives of acetophenone with substituent methoxyl, methyl, nitro and bromine in position - ortho (e.e. of 94 to > 99% conversion and 23-80%). With respect to the chlorine and fluorine substituents, the best results of selectivity and enzymatic activity were obtained for the â para substituted derivatives (e.e. 93% and 73% conversion, 83% e.e. and conversion of 51%, respectively). |
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Biblioteca Digital de Teses e Dissertações da UFC |
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info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm DyckBiorreduÃÃo de cetonas aromÃticas prÃ-quirais empregando Pseudomonas sp. isolada de Nopalea cochenellifera (L.) Salm Dyck2012-08-17Marcos Carlos de Mattos11614814864Maria da ConceiÃÃo Ferreira de Oliveira97771430791AngÃlica Maria Lucchese39684636091http://lattes.cnpq.br/584045281802431301315738376 http://lattes.cnpq.br/9803071637661522Ana Caroline Lustosa de Melo CarvalhoUniversidade Federal do CearÃPrograma de PÃs-GraduaÃÃo em QuÃmica UFCBRBiorreduÃÃo Pseudomonas sp Ãlcoois QuiraisBioreduction Pseudomonas sp Chiral alcoholsQUIMICA ORGANICAHerein we describe the study biocatalytic potential of the whole cell of microorganisms isolated from a plant belonging to Cactacea family, Nopalea cochenillifera (L.) Salm- Dyck, popularly known as âpalma doceâ or âpalma forrageiraâ. The microorganisms were isolated by induction technique using as acetophenone susbtrate. Among the microorganisms strains (I-1, I-2, I-3, I-4) only I-2, (Pseudomonas sp), was effective as biocatalyst in reducing the acetophenone. The best conditions for carrying out the bioreduction of acetophenone were as follows: 1g of resting cells of Pseudomonas sp, resuspended in buffer solution pH 7, at 28 Â C and rotation of 175 r.p.m for 4 days, obtaining the (S)-1-phenylethanol with conversion of 77% e.e. and 89%. The bioreduction study, using the Pseudomonas sp strain, was extended to the following derivatives of acetophenone, 4-methoxy-acetophenone (2a), 4-methyl acetophenone (3a), 4-nitro-acetophenone (4a), 4 -bromo-acetophenone (5a), 4-chloro-acetophenone (6a), 4-fluoro-acetophenone (7a), 3-methoxy-acetophenone (8a), 3-methyl acetophenone (9a), 3-nitro-acetophenone (10a) 2-methoxy-acetophenone (11a), 2-methyl acetophenone (12a), 2-nitro-acetophenone (13a), 2-bromo-acetophenone (14a), 2-chloro-acetophenone (15a), 2 - fluoro-acetophenone (16a). It is not worthy that all the alcohols were obtained with Prelog selectivity (S configuration). In general, the best results were obtained for the derivatives of acetophenone with substituent methoxyl, methyl, nitro and bromine in position - ortho (e.e. of 94 to > 99% conversion and 23-80%). With respect to the chlorine and fluorine substituents, the best results of selectivity and enzymatic activity were obtained for the â para substituted derivatives (e.e. 93% and 73% conversion, 83% e.e. and conversion of 51%, respectively). Neste trabalho descrevemos o estudo do potencial biocatalÃtico de cÃlulas Ãntegras de micro-organismos isolados de um vegetal da famÃlia das Cactaceas, Nopalea cochenillifera (L.) Salm-Dyck, popularmente conhecido como âpalma doceâ ou âpalma forrageiraâ. Os micro-organismos foram isolados pela tÃcnica de induÃÃo utilizando o substrato acetofenona. Dos quatro micro-organismo isolados (I-1, I-2, I-3, I-4) apenas o I-2, identificado como Pseudomonas sp, foi eficiente como biocatalisador na reduÃÃo do substrato padrÃo acetofenona. As melhores condiÃÃes para a realizaÃÃo da biorreduÃÃo da acetofenona foram as seguintes: 1g de cÃlulas em repouso de Pseudomonas sp, ressuspendidas em soluÃÃo tampÃo de pH 7, temperatura de 28 ÂC e rotaÃÃo de 175 r.p.m por 4 dias, com obtenÃÃo do (S)-1-feniletanol com conversÃo de 77% e e.e. de 89%. O estudo da biorreduÃÃo, utilizando a cepa isolada de Pseudomonas sp, foi estendido para os seguintes derivados da acetofenona: 4-metÃxi-acetofenona (2a), 4-metil-acetofenona (3a), 4-nitro-acetofenona (4a), 4-bromo-acetofenona (5a), 4-cloro-acetofenona (6a), 4-fluoro-acetofenona (7a), 3-metÃxi-acetofenona (8a), 3-metil-acetofenona (9a), 3-nitro-acetofenona (10a), 2-metÃxi-acetofenona (11a), 2-metil-acetofenona (12a), 2-nitro-acetofenona (13a), 2-bromo-acetofenona (14a), 2-cloro-acetofenona (15a), 2-fluoro-acetofenona (16a). Cabe ressaltar que todos os Ãlcoois foram obtidos com seletividade Prelog (configuraÃÃo S). Em geral, os melhores resultados foram obtidos para os derivados da acetofenona com substituintes metoxila, metila, nitro e bromo na posiÃÃo â orto (e.e. de 94 a > 99% e conversÃo de 23 a 80%). Com relaÃÃo aos substituintes cloro e flÃor, os melhores resultados de seletividade e atividade enzimÃtica foram obtidos para os derivados âpara substituÃdos (e.e. 93% e conversÃo 73%; e.e. 83% e conversÃo de 51%, respectivamente). http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=8904application/pdfinfo:eu-repo/semantics/openAccessporreponame:Biblioteca Digital de Teses e Dissertações da UFCinstname:Universidade Federal do Cearáinstacron:UFC2019-01-21T11:21:57Zmail@mail.com - |
dc.title.en.fl_str_mv |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck |
dc.title.alternative.pt.fl_str_mv |
BiorreduÃÃo de cetonas aromÃticas prÃ-quirais empregando Pseudomonas sp. isolada de Nopalea cochenellifera (L.) Salm Dyck |
title |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck |
spellingShingle |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck Ana Caroline Lustosa de Melo Carvalho BiorreduÃÃo Pseudomonas sp Ãlcoois Quirais Bioreduction Pseudomonas sp Chiral alcohols QUIMICA ORGANICA |
title_short |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck |
title_full |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck |
title_fullStr |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck |
title_full_unstemmed |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck |
title_sort |
Bioreduction of prochiral aromatic ketones using Pseudomonas sp. Nopalea cochenellifera isolated (L.) Salm Dyck |
author |
Ana Caroline Lustosa de Melo Carvalho |
author_facet |
Ana Caroline Lustosa de Melo Carvalho |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Marcos Carlos de Mattos |
dc.contributor.advisor1ID.fl_str_mv |
11614814864 |
dc.contributor.referee1.fl_str_mv |
Maria da ConceiÃÃo Ferreira de Oliveira |
dc.contributor.referee1ID.fl_str_mv |
97771430791 |
dc.contributor.referee2.fl_str_mv |
AngÃlica Maria Lucchese |
dc.contributor.referee2ID.fl_str_mv |
39684636091 |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/5840452818024313 |
dc.contributor.authorID.fl_str_mv |
01315738376 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9803071637661522 |
dc.contributor.author.fl_str_mv |
Ana Caroline Lustosa de Melo Carvalho |
contributor_str_mv |
Marcos Carlos de Mattos Maria da ConceiÃÃo Ferreira de Oliveira AngÃlica Maria Lucchese |
dc.subject.por.fl_str_mv |
BiorreduÃÃo Pseudomonas sp Ãlcoois Quirais |
topic |
BiorreduÃÃo Pseudomonas sp Ãlcoois Quirais Bioreduction Pseudomonas sp Chiral alcohols QUIMICA ORGANICA |
dc.subject.eng.fl_str_mv |
Bioreduction Pseudomonas sp Chiral alcohols |
dc.subject.cnpq.fl_str_mv |
QUIMICA ORGANICA |
dc.description.abstract.por.fl_txt_mv |
Herein we describe the study biocatalytic potential of the whole cell of microorganisms isolated from a plant belonging to Cactacea family, Nopalea cochenillifera (L.) Salm- Dyck, popularly known as âpalma doceâ or âpalma forrageiraâ. The microorganisms were isolated by induction technique using as acetophenone susbtrate. Among the microorganisms strains (I-1, I-2, I-3, I-4) only I-2, (Pseudomonas sp), was effective as biocatalyst in reducing the acetophenone. The best conditions for carrying out the bioreduction of acetophenone were as follows: 1g of resting cells of Pseudomonas sp, resuspended in buffer solution pH 7, at 28 Â C and rotation of 175 r.p.m for 4 days, obtaining the (S)-1-phenylethanol with conversion of 77% e.e. and 89%. The bioreduction study, using the Pseudomonas sp strain, was extended to the following derivatives of acetophenone, 4-methoxy-acetophenone (2a), 4-methyl acetophenone (3a), 4-nitro-acetophenone (4a), 4 -bromo-acetophenone (5a), 4-chloro-acetophenone (6a), 4-fluoro-acetophenone (7a), 3-methoxy-acetophenone (8a), 3-methyl acetophenone (9a), 3-nitro-acetophenone (10a) 2-methoxy-acetophenone (11a), 2-methyl acetophenone (12a), 2-nitro-acetophenone (13a), 2-bromo-acetophenone (14a), 2-chloro-acetophenone (15a), 2 - fluoro-acetophenone (16a). It is not worthy that all the alcohols were obtained with Prelog selectivity (S configuration). In general, the best results were obtained for the derivatives of acetophenone with substituent methoxyl, methyl, nitro and bromine in position - ortho (e.e. of 94 to > 99% conversion and 23-80%). With respect to the chlorine and fluorine substituents, the best results of selectivity and enzymatic activity were obtained for the â para substituted derivatives (e.e. 93% and 73% conversion, 83% e.e. and conversion of 51%, respectively). Neste trabalho descrevemos o estudo do potencial biocatalÃtico de cÃlulas Ãntegras de micro-organismos isolados de um vegetal da famÃlia das Cactaceas, Nopalea cochenillifera (L.) Salm-Dyck, popularmente conhecido como âpalma doceâ ou âpalma forrageiraâ. Os micro-organismos foram isolados pela tÃcnica de induÃÃo utilizando o substrato acetofenona. Dos quatro micro-organismo isolados (I-1, I-2, I-3, I-4) apenas o I-2, identificado como Pseudomonas sp, foi eficiente como biocatalisador na reduÃÃo do substrato padrÃo acetofenona. As melhores condiÃÃes para a realizaÃÃo da biorreduÃÃo da acetofenona foram as seguintes: 1g de cÃlulas em repouso de Pseudomonas sp, ressuspendidas em soluÃÃo tampÃo de pH 7, temperatura de 28 ÂC e rotaÃÃo de 175 r.p.m por 4 dias, com obtenÃÃo do (S)-1-feniletanol com conversÃo de 77% e e.e. de 89%. O estudo da biorreduÃÃo, utilizando a cepa isolada de Pseudomonas sp, foi estendido para os seguintes derivados da acetofenona: 4-metÃxi-acetofenona (2a), 4-metil-acetofenona (3a), 4-nitro-acetofenona (4a), 4-bromo-acetofenona (5a), 4-cloro-acetofenona (6a), 4-fluoro-acetofenona (7a), 3-metÃxi-acetofenona (8a), 3-metil-acetofenona (9a), 3-nitro-acetofenona (10a), 2-metÃxi-acetofenona (11a), 2-metil-acetofenona (12a), 2-nitro-acetofenona (13a), 2-bromo-acetofenona (14a), 2-cloro-acetofenona (15a), 2-fluoro-acetofenona (16a). Cabe ressaltar que todos os Ãlcoois foram obtidos com seletividade Prelog (configuraÃÃo S). Em geral, os melhores resultados foram obtidos para os derivados da acetofenona com substituintes metoxila, metila, nitro e bromo na posiÃÃo â orto (e.e. de 94 a > 99% e conversÃo de 23 a 80%). Com relaÃÃo aos substituintes cloro e flÃor, os melhores resultados de seletividade e atividade enzimÃtica foram obtidos para os derivados âpara substituÃdos (e.e. 93% e conversÃo 73%; e.e. 83% e conversÃo de 51%, respectivamente). |
description |
Herein we describe the study biocatalytic potential of the whole cell of microorganisms isolated from a plant belonging to Cactacea family, Nopalea cochenillifera (L.) Salm- Dyck, popularly known as âpalma doceâ or âpalma forrageiraâ. The microorganisms were isolated by induction technique using as acetophenone susbtrate. Among the microorganisms strains (I-1, I-2, I-3, I-4) only I-2, (Pseudomonas sp), was effective as biocatalyst in reducing the acetophenone. The best conditions for carrying out the bioreduction of acetophenone were as follows: 1g of resting cells of Pseudomonas sp, resuspended in buffer solution pH 7, at 28 Â C and rotation of 175 r.p.m for 4 days, obtaining the (S)-1-phenylethanol with conversion of 77% e.e. and 89%. The bioreduction study, using the Pseudomonas sp strain, was extended to the following derivatives of acetophenone, 4-methoxy-acetophenone (2a), 4-methyl acetophenone (3a), 4-nitro-acetophenone (4a), 4 -bromo-acetophenone (5a), 4-chloro-acetophenone (6a), 4-fluoro-acetophenone (7a), 3-methoxy-acetophenone (8a), 3-methyl acetophenone (9a), 3-nitro-acetophenone (10a) 2-methoxy-acetophenone (11a), 2-methyl acetophenone (12a), 2-nitro-acetophenone (13a), 2-bromo-acetophenone (14a), 2-chloro-acetophenone (15a), 2 - fluoro-acetophenone (16a). It is not worthy that all the alcohols were obtained with Prelog selectivity (S configuration). In general, the best results were obtained for the derivatives of acetophenone with substituent methoxyl, methyl, nitro and bromine in position - ortho (e.e. of 94 to > 99% conversion and 23-80%). With respect to the chlorine and fluorine substituents, the best results of selectivity and enzymatic activity were obtained for the â para substituted derivatives (e.e. 93% and 73% conversion, 83% e.e. and conversion of 51%, respectively). |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012-08-17 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
status_str |
publishedVersion |
format |
masterThesis |
dc.identifier.uri.fl_str_mv |
http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=8904 |
url |
http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=8904 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal do Cearà |
dc.publisher.program.fl_str_mv |
Programa de PÃs-GraduaÃÃo em QuÃmica |
dc.publisher.initials.fl_str_mv |
UFC |
dc.publisher.country.fl_str_mv |
BR |
publisher.none.fl_str_mv |
Universidade Federal do Cearà |
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reponame:Biblioteca Digital de Teses e Dissertações da UFC instname:Universidade Federal do Ceará instacron:UFC |
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Biblioteca Digital de Teses e Dissertações da UFC |
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Biblioteca Digital de Teses e Dissertações da UFC |
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Universidade Federal do Ceará |
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UFC |
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UFC |
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mail@mail.com |
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