Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach
Main Author: | |
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Publication Date: | 2014 |
Format: | Master thesis |
Language: | por |
Source: | Repositório Institucional da UFSCAR |
Download full: | https://repositorio.ufscar.br/handle/ufscar/6610 |
Summary: | Endophytic microorganisms have a great enzymatic potential to biotransformate substances of natural and synthetic origin due to strategies developed during colonization to coexist with the plant in an initial hostile environment. Microbial transformation of Diels-Alder cycloadducts were trailed by the endophyte P. brasilianum using intact cells and resulted in the production of several products (17). These products were identified as products of chlorination (Q4_F2_15), epoxidation (Q1A_CR_16, Q2A_CR_6, Q3A_CR_5), epoxidation and reduction of conjugated double bond (Q2A_CR_5), reduction of conjugated double bond (Q2A_CR_9, Q3A_CR_7_pico2, Q3A_CR_8, Q4A_CR_23), reduction of isolated double bond (Q1A_CR_26), oxidation of allilic methyl group and reduction of conjugated double bond (Q4A_CR_10), reduction of carbonyl and conjugated double bond (Q4A_CR_20), reduction of carbonyl and ether formation (Q5A_CR_15) and finally, reduction of carbonyl group (Q4A_CR_15 e Q5A_CR_18). The reduction of conjugated double bond can be performed by enzymes called Old Yellow Enzymes (OYE), also known as enoate reductase enzymes. The products of carbonilic or double bond reduction were also synthesized chemically and the enantioselectivity of both in vitro and in vivo process were compared. In all cases, microbiological transformations were more enantioselectivity. |
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Santos, Ana Carolina Alves dosRodrigues Filho, Edsonhttp://lattes.cnpq.br/3667941735597178http://lattes.cnpq.br/61690452303741292016-06-02T20:36:55Z2015-03-102016-06-02T20:36:55Z2014-03-27SANTOS, Ana Carolina Alves dos. Biotransformation of Diels-Alder cycloadducts using intacts cell by Penicillium brasilianum, an endophyte isolated from Melia azedarach. 2014. 196 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014.https://repositorio.ufscar.br/handle/ufscar/6610Endophytic microorganisms have a great enzymatic potential to biotransformate substances of natural and synthetic origin due to strategies developed during colonization to coexist with the plant in an initial hostile environment. Microbial transformation of Diels-Alder cycloadducts were trailed by the endophyte P. brasilianum using intact cells and resulted in the production of several products (17). These products were identified as products of chlorination (Q4_F2_15), epoxidation (Q1A_CR_16, Q2A_CR_6, Q3A_CR_5), epoxidation and reduction of conjugated double bond (Q2A_CR_5), reduction of conjugated double bond (Q2A_CR_9, Q3A_CR_7_pico2, Q3A_CR_8, Q4A_CR_23), reduction of isolated double bond (Q1A_CR_26), oxidation of allilic methyl group and reduction of conjugated double bond (Q4A_CR_10), reduction of carbonyl and conjugated double bond (Q4A_CR_20), reduction of carbonyl and ether formation (Q5A_CR_15) and finally, reduction of carbonyl group (Q4A_CR_15 e Q5A_CR_18). The reduction of conjugated double bond can be performed by enzymes called Old Yellow Enzymes (OYE), also known as enoate reductase enzymes. The products of carbonilic or double bond reduction were also synthesized chemically and the enantioselectivity of both in vitro and in vivo process were compared. In all cases, microbiological transformations were more enantioselectivity.Devido às estratégias usadas para a colonização do hospedeiro e à convivência com a planta em um ambiente inicialmente hostil, os micro-organismos endofíticos possuem um grande potencial enzimático para biotransformar substâncias de origem natural e seus análogos sintéticos. A transformação dos cicloadutos de Diels-Alder feitas pelo endofítico P. brasilianum utilizando-se células intactas resultou na produção de 17 produtos de biotransformação. Esses produtos foram identificados como sendo produtos de halogenação (Q4_F2_15), epoxidação (Q1A_CR_16, Q2A_CR_6, Q3A_CR_5), epoxidação e redução da olefina conjugada (Q2A_CR_5), redução da dupla ligação α, β- insaturada (Q2A_CR_9, Q3A_CR_7_pico2, Q3A_CR_8, Q4A_CR_23), redução da olefina isolada (Q1A_CR_26), oxidação alílica de metila e redução da dupla conjugada (Q4A_CR_10), redução carbonílica e dupla conjugada (Q4A_CR_20), redução carbonílica e formação de éter (Q5A_CR_15) e redução de grupos carbonílicos (Q4A_CR_15 e Q5A_CR_18). As reduções das olefinas pertencentes ao sistema α, β- insaturada podem ter sido catalisadas por enzimas da família Old Yellow Enzymes (OYE), também conhecidas por enoato redutases. Os produtos de redução C=C do sistema α, β- insaturado e redução carbonílica também foram sintetizados quimicamente e a enantiosseletividade de ambos os processos foram comparadas. Em todos os casos, as transformações microbiológicas apresentaram uma maior enantiosseletividade.Financiadora de Estudos e Projetosapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRMicroorganismos endofíticosPenicillium brasilianumBiotransformaçãoCélulas intactasDiels-AlderCIENCIAS EXATAS E DA TERRA::QUIMICABiotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarachBiotransformation of Diels-Alder cycloadducts using intacts cell by Penicillium brasilianum, an endophyte isolated from Melia azedarachinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINAL6548.pdfapplication/pdf4383232https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/6610/1/6548.pdf8fc19ea524835c26efc13265b5ea37adMD51TEXT6548.pdf.txt6548.pdf.txtExtracted texttext/plain0https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/6610/2/6548.pdf.txtd41d8cd98f00b204e9800998ecf8427eMD52THUMBNAIL6548.pdf.jpg6548.pdf.jpgIM Thumbnailimage/jpeg10245https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/6610/3/6548.pdf.jpge0e494bf81687b9359665a5d095c3f46MD53ufscar/66102019-09-11 03:52:18.065oai:repositorio.ufscar.br:ufscar/6610Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222019-09-11T03:52:18Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach |
dc.title.alternative.eng.fl_str_mv |
Biotransformation of Diels-Alder cycloadducts using intacts cell by Penicillium brasilianum, an endophyte isolated from Melia azedarach |
title |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach |
spellingShingle |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach Santos, Ana Carolina Alves dos Microorganismos endofíticos Penicillium brasilianum Biotransformação Células intactas Diels-Alder CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach |
title_full |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach |
title_fullStr |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach |
title_full_unstemmed |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach |
title_sort |
Biotransformação de cicloadutos de Diels-Alder por células intactas de Penicillium brasilianum, endofítico de Melia azedarach |
author |
Santos, Ana Carolina Alves dos |
author_facet |
Santos, Ana Carolina Alves dos |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/6169045230374129 |
dc.contributor.author.fl_str_mv |
Santos, Ana Carolina Alves dos |
dc.contributor.advisor1.fl_str_mv |
Rodrigues Filho, Edson |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3667941735597178 |
contributor_str_mv |
Rodrigues Filho, Edson |
dc.subject.por.fl_str_mv |
Microorganismos endofíticos Penicillium brasilianum Biotransformação Células intactas Diels-Alder |
topic |
Microorganismos endofíticos Penicillium brasilianum Biotransformação Células intactas Diels-Alder CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Endophytic microorganisms have a great enzymatic potential to biotransformate substances of natural and synthetic origin due to strategies developed during colonization to coexist with the plant in an initial hostile environment. Microbial transformation of Diels-Alder cycloadducts were trailed by the endophyte P. brasilianum using intact cells and resulted in the production of several products (17). These products were identified as products of chlorination (Q4_F2_15), epoxidation (Q1A_CR_16, Q2A_CR_6, Q3A_CR_5), epoxidation and reduction of conjugated double bond (Q2A_CR_5), reduction of conjugated double bond (Q2A_CR_9, Q3A_CR_7_pico2, Q3A_CR_8, Q4A_CR_23), reduction of isolated double bond (Q1A_CR_26), oxidation of allilic methyl group and reduction of conjugated double bond (Q4A_CR_10), reduction of carbonyl and conjugated double bond (Q4A_CR_20), reduction of carbonyl and ether formation (Q5A_CR_15) and finally, reduction of carbonyl group (Q4A_CR_15 e Q5A_CR_18). The reduction of conjugated double bond can be performed by enzymes called Old Yellow Enzymes (OYE), also known as enoate reductase enzymes. The products of carbonilic or double bond reduction were also synthesized chemically and the enantioselectivity of both in vitro and in vivo process were compared. In all cases, microbiological transformations were more enantioselectivity. |
publishDate |
2014 |
dc.date.issued.fl_str_mv |
2014-03-27 |
dc.date.available.fl_str_mv |
2015-03-10 2016-06-02T20:36:55Z |
dc.date.accessioned.fl_str_mv |
2016-06-02T20:36:55Z |
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 |
SANTOS, Ana Carolina Alves dos. Biotransformation of Diels-Alder cycloadducts using intacts cell by Penicillium brasilianum, an endophyte isolated from Melia azedarach. 2014. 196 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/6610 |
identifier_str_mv |
SANTOS, Ana Carolina Alves dos. Biotransformation of Diels-Alder cycloadducts using intacts cell by Penicillium brasilianum, an endophyte isolated from Melia azedarach. 2014. 196 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014. |
url |
https://repositorio.ufscar.br/handle/ufscar/6610 |
dc.language.iso.fl_str_mv |
por |
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por |
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openAccess |
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application/pdf |
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Universidade Federal de São Carlos |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química - PPGQ |
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UFSCar |
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BR |
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Universidade Federal de São Carlos |
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