Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , |
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=S0103-50532019000400772 |
Resumo: | A biocatalytic cascade process was developed using immobilized cells of the wild type yeast Candida albicans CCT 0776 in calcium alginate beads and a commercially available ketoreductase. The aim was to promote deracemization by stereoinversion of (±)-1-arylethanols in high substrate concentration (above 100 mmol L-1) to prepare the (R)-enantiomers of the alcohols (90-99%), with a high enantiomeric excess (83-99%) after 2 to 19 h. The (R)-1-(3-methoxyphenyl)ethanol, with 70% yield and 91% ee, obtained after 5 h was used to prepare (S)-1-(3-methoxyphenyl)-ethylamine with 60% yield and 91% ee after two steps, a key intermediate in the synthesis of (S)-rivastigmine. |
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Journal of the Brazilian Chemical Society (Online) |
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Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductasesoxidative kinetic resolutionderacemizationstereoinversionketoreductasealcohol dehydrogenaseA biocatalytic cascade process was developed using immobilized cells of the wild type yeast Candida albicans CCT 0776 in calcium alginate beads and a commercially available ketoreductase. The aim was to promote deracemization by stereoinversion of (±)-1-arylethanols in high substrate concentration (above 100 mmol L-1) to prepare the (R)-enantiomers of the alcohols (90-99%), with a high enantiomeric excess (83-99%) after 2 to 19 h. The (R)-1-(3-methoxyphenyl)ethanol, with 70% yield and 91% ee, obtained after 5 h was used to prepare (S)-1-(3-methoxyphenyl)-ethylamine with 60% yield and 91% ee after two steps, a key intermediate in the synthesis of (S)-rivastigmine.Sociedade Brasileira de Química2019-04-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000400772Journal of the Brazilian Chemical Society v.30 n.4 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20180205info:eu-repo/semantics/openAccessNasário,Fábio D.Moran,Paulo J. S.Rodrigues,José Augusto R.eng2019-03-12T00:00:00Zoai:scielo:S0103-50532019000400772Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-03-12T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases |
title |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases |
spellingShingle |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases Nasário,Fábio D. oxidative kinetic resolution deracemization stereoinversion ketoreductase alcohol dehydrogenase |
title_short |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases |
title_full |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases |
title_fullStr |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases |
title_full_unstemmed |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases |
title_sort |
Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases |
author |
Nasário,Fábio D. |
author_facet |
Nasário,Fábio D. Moran,Paulo J. S. Rodrigues,José Augusto R. |
author_role |
author |
author2 |
Moran,Paulo J. S. Rodrigues,José Augusto R. |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Nasário,Fábio D. Moran,Paulo J. S. Rodrigues,José Augusto R. |
dc.subject.por.fl_str_mv |
oxidative kinetic resolution deracemization stereoinversion ketoreductase alcohol dehydrogenase |
topic |
oxidative kinetic resolution deracemization stereoinversion ketoreductase alcohol dehydrogenase |
description |
A biocatalytic cascade process was developed using immobilized cells of the wild type yeast Candida albicans CCT 0776 in calcium alginate beads and a commercially available ketoreductase. The aim was to promote deracemization by stereoinversion of (±)-1-arylethanols in high substrate concentration (above 100 mmol L-1) to prepare the (R)-enantiomers of the alcohols (90-99%), with a high enantiomeric excess (83-99%) after 2 to 19 h. The (R)-1-(3-methoxyphenyl)ethanol, with 70% yield and 91% ee, obtained after 5 h was used to prepare (S)-1-(3-methoxyphenyl)-ethylamine with 60% yield and 91% ee after two steps, a key intermediate in the synthesis of (S)-rivastigmine. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-04-01 |
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=S0103-50532019000400772 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000400772 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20180205 |
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.30 n.4 2019 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 |
_version_ |
1750318181681987584 |