Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica

The lipase B from Candida antarctica (Novozym 435(®), CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enant...

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Autores principales: Ferreira, Hercules V., Rocha, Lenilson C., Severino, Richele P., Porto, André L. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268719/
https://www.ncbi.nlm.nih.gov/pubmed/22836214
http://dx.doi.org/10.3390/molecules17088955
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author Ferreira, Hercules V.
Rocha, Lenilson C.
Severino, Richele P.
Porto, André L. M.
author_facet Ferreira, Hercules V.
Rocha, Lenilson C.
Severino, Richele P.
Porto, André L. M.
author_sort Ferreira, Hercules V.
collection PubMed
description The lipase B from Candida antarctica (Novozym 435(®), CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.
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spelling pubmed-62687192018-12-12 Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica Ferreira, Hercules V. Rocha, Lenilson C. Severino, Richele P. Porto, André L. M. Molecules Article The lipase B from Candida antarctica (Novozym 435(®), CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent. MDPI 2012-07-26 /pmc/articles/PMC6268719/ /pubmed/22836214 http://dx.doi.org/10.3390/molecules17088955 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Ferreira, Hercules V.
Rocha, Lenilson C.
Severino, Richele P.
Porto, André L. M.
Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_full Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_fullStr Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_full_unstemmed Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_short Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_sort syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase b from candida antarctica
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268719/
https://www.ncbi.nlm.nih.gov/pubmed/22836214
http://dx.doi.org/10.3390/molecules17088955
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