The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases

Detalhes bibliográficos
Autor(a) principal: Silva,Julyetty Crystyne da
Data de Publicação: 2016
Outros Autores: Nascimento,Maria da Graça
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202226
Resumo: In this study, various commercial and native lipases, free or immobilized, were used in the enantioselective resolution of (R,S)-menthol with vinyl acetate for the preparation of menthyl acetate. Lipase from Candida rugosa (AYL) was found to be the most appropriate. When the reaction was carried out at 35 ºC, using 40 mg of AYL and a molar ratio of 1:2 (alcohol:ester), the values for the conversion degree, the enantiomeric excess of the substrate (ees) and product (eep) and the enantiomeric ratio (E) were 33.6, 50.3, > 99% and > 200, respectively. The results showed that the reaction was more efficient using toluene in comparison with other organic solvents or mixtures of toluene and ionic liquids (ILs). The best support for the AYL immobilization, was corn starch film. This system was used 4 times over 71 days of storage, and menthyl acetate was still obtained with good values of conversion degree, ees, eep, and E.
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spelling The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipaseslipaseimmobilizationstarch filmenzymatic kinetic resolution(R,S)-mentholIn this study, various commercial and native lipases, free or immobilized, were used in the enantioselective resolution of (R,S)-menthol with vinyl acetate for the preparation of menthyl acetate. Lipase from Candida rugosa (AYL) was found to be the most appropriate. When the reaction was carried out at 35 ºC, using 40 mg of AYL and a molar ratio of 1:2 (alcohol:ester), the values for the conversion degree, the enantiomeric excess of the substrate (ees) and product (eep) and the enantiomeric ratio (E) were 33.6, 50.3, > 99% and > 200, respectively. The results showed that the reaction was more efficient using toluene in comparison with other organic solvents or mixtures of toluene and ionic liquids (ILs). The best support for the AYL immobilization, was corn starch film. This system was used 4 times over 71 days of storage, and menthyl acetate was still obtained with good values of conversion degree, ees, eep, and E.Sociedade Brasileira de Química2016-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202226Journal of the Brazilian Chemical Society v.27 n.12 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160115info:eu-repo/semantics/openAccessSilva,Julyetty Crystyne daNascimento,Maria da Graçaeng2016-12-01T00:00:00Zoai:scielo:S0103-50532016001202226Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-12-01T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
title The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
spellingShingle The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
Silva,Julyetty Crystyne da
lipase
immobilization
starch film
enzymatic kinetic resolution
(R,S)-menthol
title_short The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
title_full The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
title_fullStr The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
title_full_unstemmed The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
title_sort The Influence of Organic Medium and Supports in the Resolution of (R,S)-Menthol Catalyzed by Lipases
author Silva,Julyetty Crystyne da
author_facet Silva,Julyetty Crystyne da
Nascimento,Maria da Graça
author_role author
author2 Nascimento,Maria da Graça
author2_role author
dc.contributor.author.fl_str_mv Silva,Julyetty Crystyne da
Nascimento,Maria da Graça
dc.subject.por.fl_str_mv lipase
immobilization
starch film
enzymatic kinetic resolution
(R,S)-menthol
topic lipase
immobilization
starch film
enzymatic kinetic resolution
(R,S)-menthol
description In this study, various commercial and native lipases, free or immobilized, were used in the enantioselective resolution of (R,S)-menthol with vinyl acetate for the preparation of menthyl acetate. Lipase from Candida rugosa (AYL) was found to be the most appropriate. When the reaction was carried out at 35 ºC, using 40 mg of AYL and a molar ratio of 1:2 (alcohol:ester), the values for the conversion degree, the enantiomeric excess of the substrate (ees) and product (eep) and the enantiomeric ratio (E) were 33.6, 50.3, > 99% and > 200, respectively. The results showed that the reaction was more efficient using toluene in comparison with other organic solvents or mixtures of toluene and ionic liquids (ILs). The best support for the AYL immobilization, was corn starch film. This system was used 4 times over 71 days of storage, and menthyl acetate was still obtained with good values of conversion degree, ees, eep, and E.
publishDate 2016
dc.date.none.fl_str_mv 2016-12-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202226
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202226
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20160115
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.27 n.12 2016
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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