Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina

Detalhes bibliográficos
Autor(a) principal: Marcos Reinaldo da Silva
Data de Publicação: 2014
Tipo de documento: Tese
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=13920
Resumo: The present work is divided into three chapters, in which we report the use of lipases to obtain precursors of α-amino acid, derivatives thiamphenicol and chemoenzymatic synthesis of (S)-dapoxetine. The first chapter refers to the use of the lipase from Rhyzomucor miehei, which by means of kinetic resolution of N-acetyl-α-amino esters was possible to obtain derivatives with high values of enantiomeric excesses. The second section aims at obtaining derivatives of thiamphenicol applying the lipase from Candida rugosa for the reaction of hydrolysis of the diacetate thiamphenicol, and Candida antarctica lipase B by acylation process. Finally, the third section reports the chemoenzymatic synthesis of (S)-dapoxetine in the enantiopure form by kinetic resolution process via transesterification reactions of 3-chloro-1-phenylpropan-1-ol, using lipase from Candida rugosa.
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spelling info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBiocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetinaProcessos biocatalÃticos na obtenÃÃo de produtos com alto valor agregado: sÃnteses quimioenzimÃticas de α- aminoÃcidos, derivados do tianfenicol e (S)-dapoxetina.2014-02-28Marcos Carlos de Mattos11614814864Telma Leda Gomes de Lemos04511700320http://buscatextual.cnpq.br/buscatextual/visualizacv.jsp?id=K4783204Z7Maria da ConceiÃÃo Ferreira de Oliveira97771430791AngÃlica Maria Lucchese39684636091http://lattes.cnpq.br/5840452818024313Liliana Marzorati6110522880001063126347http://lattes.cnpq.br/9852260171953866 Marcos Reinaldo da SilvaUniversidade Federal do CearÃPrograma de PÃs-GraduaÃÃo em QuÃmica UFCBRLipasesAminoÃcidosResoluÃÃo cinÃticaTianfenicolLipasesAminoacidsKinetic resolutionThiamphenicolQUIMICA ORGANICAThe present work is divided into three chapters, in which we report the use of lipases to obtain precursors of α-amino acid, derivatives thiamphenicol and chemoenzymatic synthesis of (S)-dapoxetine. The first chapter refers to the use of the lipase from Rhyzomucor miehei, which by means of kinetic resolution of N-acetyl-α-amino esters was possible to obtain derivatives with high values of enantiomeric excesses. The second section aims at obtaining derivatives of thiamphenicol applying the lipase from Candida rugosa for the reaction of hydrolysis of the diacetate thiamphenicol, and Candida antarctica lipase B by acylation process. Finally, the third section reports the chemoenzymatic synthesis of (S)-dapoxetine in the enantiopure form by kinetic resolution process via transesterification reactions of 3-chloro-1-phenylpropan-1-ol, using lipase from Candida rugosa.O presente trabalho encontra-se dividido em trÃs capÃtulos, na qual relatamos a utilizaÃÃo de lipases para obtenÃÃo de precursores de α-aminoÃcidos, derivados de tianfenicol e a sÃntese quimioenzimÃtica da (S)-dapoxetina. O primeiro capÃtulo refere-se à utilizaÃÃo da lipase a partir de Rhyzomucor miehei, que por meio de uma resoluÃÃo cinÃtica de N-acetil-α-aminoÃsteres foi possÃvel obter derivados com elevados valores de excessos enantiomÃricos. O segundo capÃtulo visa a obtenÃÃo de derivados do tianfenicol aplicando a lipase a partir da Candida rugosa para a reaÃÃo de hidrÃlise do diacetato de tianfenicol, e a lipase B obtida a partir de Candida antarctica por processo de acilaÃÃo. Por fim, o terceiro capÃtulo relata a sÃntese quimioenzimÃtica da (S)-dapoxetina de forma enantiopura por processo de resoluÃÃo cinÃtica via reaÃÃes de transesterificaÃÃo do 3-cloro-1-fenilpropan-1-ol, usando a lipase obtida a partir da Candida rugosa.CoordenaÃÃo de AperfeiÃoamento de Pessoal de NÃvel Superiorhttp://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13920application/pdfinfo:eu-repo/semantics/openAccessporreponame:Biblioteca Digital de Teses e Dissertações da UFCinstname:Universidade Federal do Cearáinstacron:UFC2019-01-21T11:28:43Zmail@mail.com -
dc.title.en.fl_str_mv Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
dc.title.alternative.pt.fl_str_mv Processos biocatalÃticos na obtenÃÃo de produtos com alto valor agregado: sÃnteses quimioenzimÃticas de α- aminoÃcidos, derivados do tianfenicol e (S)-dapoxetina.
title Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
spellingShingle Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
Marcos Reinaldo da Silva
Lipases
AminoÃcidos
ResoluÃÃo cinÃtica
Tianfenicol
Lipases
Aminoacids
Kinetic resolution
Thiamphenicol
QUIMICA ORGANICA
title_short Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
title_full Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
title_fullStr Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
title_full_unstemmed Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
title_sort Biocatalytic processin obtaining products with high added value: chemoenzymatic synthesis of α-amino acids, derivates thiamphenicol and (S)-dapoxetina
author Marcos Reinaldo da Silva
author_facet Marcos Reinaldo da Silva
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 Telma Leda Gomes de Lemos
dc.contributor.referee1ID.fl_str_mv 04511700320
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.jsp?id=K4783204Z7
dc.contributor.referee2.fl_str_mv Maria da ConceiÃÃo Ferreira de Oliveira
dc.contributor.referee2ID.fl_str_mv 97771430791
dc.contributor.referee3.fl_str_mv AngÃlica Maria Lucchese
dc.contributor.referee3ID.fl_str_mv 39684636091
dc.contributor.referee3Lattes.fl_str_mv http://lattes.cnpq.br/5840452818024313
dc.contributor.referee4.fl_str_mv Liliana Marzorati
dc.contributor.referee4ID.fl_str_mv 61105228800
dc.contributor.authorID.fl_str_mv 01063126347
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/9852260171953866
dc.contributor.author.fl_str_mv Marcos Reinaldo da Silva
contributor_str_mv Marcos Carlos de Mattos
Telma Leda Gomes de Lemos
Maria da ConceiÃÃo Ferreira de Oliveira
AngÃlica Maria Lucchese
Liliana Marzorati
dc.subject.por.fl_str_mv Lipases
AminoÃcidos
ResoluÃÃo cinÃtica
Tianfenicol
topic Lipases
AminoÃcidos
ResoluÃÃo cinÃtica
Tianfenicol
Lipases
Aminoacids
Kinetic resolution
Thiamphenicol
QUIMICA ORGANICA
dc.subject.eng.fl_str_mv Lipases
Aminoacids
Kinetic resolution
Thiamphenicol
dc.subject.cnpq.fl_str_mv QUIMICA ORGANICA
dc.description.sponsorship.fl_txt_mv CoordenaÃÃo de AperfeiÃoamento de Pessoal de NÃvel Superior
dc.description.abstract.por.fl_txt_mv The present work is divided into three chapters, in which we report the use of lipases to obtain precursors of α-amino acid, derivatives thiamphenicol and chemoenzymatic synthesis of (S)-dapoxetine. The first chapter refers to the use of the lipase from Rhyzomucor miehei, which by means of kinetic resolution of N-acetyl-α-amino esters was possible to obtain derivatives with high values of enantiomeric excesses. The second section aims at obtaining derivatives of thiamphenicol applying the lipase from Candida rugosa for the reaction of hydrolysis of the diacetate thiamphenicol, and Candida antarctica lipase B by acylation process. Finally, the third section reports the chemoenzymatic synthesis of (S)-dapoxetine in the enantiopure form by kinetic resolution process via transesterification reactions of 3-chloro-1-phenylpropan-1-ol, using lipase from Candida rugosa.
O presente trabalho encontra-se dividido em trÃs capÃtulos, na qual relatamos a utilizaÃÃo de lipases para obtenÃÃo de precursores de α-aminoÃcidos, derivados de tianfenicol e a sÃntese quimioenzimÃtica da (S)-dapoxetina. O primeiro capÃtulo refere-se à utilizaÃÃo da lipase a partir de Rhyzomucor miehei, que por meio de uma resoluÃÃo cinÃtica de N-acetil-α-aminoÃsteres foi possÃvel obter derivados com elevados valores de excessos enantiomÃricos. O segundo capÃtulo visa a obtenÃÃo de derivados do tianfenicol aplicando a lipase a partir da Candida rugosa para a reaÃÃo de hidrÃlise do diacetato de tianfenicol, e a lipase B obtida a partir de Candida antarctica por processo de acilaÃÃo. Por fim, o terceiro capÃtulo relata a sÃntese quimioenzimÃtica da (S)-dapoxetina de forma enantiopura por processo de resoluÃÃo cinÃtica via reaÃÃes de transesterificaÃÃo do 3-cloro-1-fenilpropan-1-ol, usando a lipase obtida a partir da Candida rugosa.
description The present work is divided into three chapters, in which we report the use of lipases to obtain precursors of α-amino acid, derivatives thiamphenicol and chemoenzymatic synthesis of (S)-dapoxetine. The first chapter refers to the use of the lipase from Rhyzomucor miehei, which by means of kinetic resolution of N-acetyl-α-amino esters was possible to obtain derivatives with high values of enantiomeric excesses. The second section aims at obtaining derivatives of thiamphenicol applying the lipase from Candida rugosa for the reaction of hydrolysis of the diacetate thiamphenicol, and Candida antarctica lipase B by acylation process. Finally, the third section reports the chemoenzymatic synthesis of (S)-dapoxetine in the enantiopure form by kinetic resolution process via transesterification reactions of 3-chloro-1-phenylpropan-1-ol, using lipase from Candida rugosa.
publishDate 2014
dc.date.issued.fl_str_mv 2014-02-28
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/doctoralThesis
status_str publishedVersion
format doctoralThesis
dc.identifier.uri.fl_str_mv http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13920
url http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13920
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 CearÃ
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 CearÃ
dc.source.none.fl_str_mv reponame:Biblioteca Digital de Teses e Dissertações da UFC
instname:Universidade Federal do Ceará
instacron:UFC
reponame_str Biblioteca Digital de Teses e Dissertações da UFC
collection Biblioteca Digital de Teses e Dissertações da UFC
instname_str Universidade Federal do Ceará
instacron_str UFC
institution UFC
repository.name.fl_str_mv -
repository.mail.fl_str_mv mail@mail.com
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