Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol
The enzymatic kinetic resolution of (RS)-trans-4-phenyl-3-butene-2-ol was investigated by screening a range of lipases both for enantioselective transesterification and for enantioselective hydrolysis of its acetate. The lipase from Pseudomonas cepacia immobilized on diatomaceous earth (PSL-D)-catal...
Published in: | Tetrahedron: Asymmetry |
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Online Access: | https://researchprofiles.canberra.edu.au/en/publications/e077a474-4d80-4450-92d0-ac8dac8bf6de https://doi.org/10.1016/S0957-4166(02)00745-0 https://researchsystem.canberra.edu.au/ws/files/26895630/Article.pdf http://www.scopus.com/inward/record.url?scp=0037421232&partnerID=8YFLogxK |
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ftcanberrauncris:oai:pure.atira.dk:publications/e077a474-4d80-4450-92d0-ac8dac8bf6de 2024-05-12T07:56:19+00:00 Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol Ghanem, Ashraf Schurig, Volker 2003-01-06 application/pdf https://researchprofiles.canberra.edu.au/en/publications/e077a474-4d80-4450-92d0-ac8dac8bf6de https://doi.org/10.1016/S0957-4166(02)00745-0 https://researchsystem.canberra.edu.au/ws/files/26895630/Article.pdf http://www.scopus.com/inward/record.url?scp=0037421232&partnerID=8YFLogxK eng eng info:eu-repo/semantics/closedAccess Ghanem , A & Schurig , V 2003 , ' Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol ' , Tetrahedron Asymmetry , vol. 14 , no. 1 , pp. 57-62 . https://doi.org/10.1016/S0957-4166(02)00745-0 article 2003 ftcanberrauncris https://doi.org/10.1016/S0957-4166(02)00745-0 2024-04-16T02:43:41Z The enzymatic kinetic resolution of (RS)-trans-4-phenyl-3-butene-2-ol was investigated by screening a range of lipases both for enantioselective transesterification and for enantioselective hydrolysis of its acetate. The lipase from Pseudomonas cepacia immobilized on diatomaceous earth (PSL-D)-catalyzed asymmetric transesterification was performed on gram scale using isopropenyl acetate as an innocuous acyl donor in organic media affording the (S)-alcohol in high enantiomeric excess (>99% ee) and enantiomeric ratio E >150. The lipase (Candida antarctica B, CAL-B)-catalyzed asymmetric hydrolysis of the racemic acetate was performed on gram scale in phosphate buffer affording the (R)-alcohol in high enantiomeric excess (>99% ee) and enantiomeric ratio E >150. The investigation demonstrates that the transesterification of the racemic alcohol in organic solvent was faster than the hydrolysis of the corresponding acetate in phosphate buffer. A GC method was developed to achieve an effective analytical separation of the enantiomers of both substrate and product in one analysis using the chiral stationary phase heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin. Article in Journal/Newspaper Antarc* Antarctica University of Canberra Research Portal Tetrahedron: Asymmetry 14 1 57 62 |
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University of Canberra Research Portal |
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ftcanberrauncris |
language |
English |
description |
The enzymatic kinetic resolution of (RS)-trans-4-phenyl-3-butene-2-ol was investigated by screening a range of lipases both for enantioselective transesterification and for enantioselective hydrolysis of its acetate. The lipase from Pseudomonas cepacia immobilized on diatomaceous earth (PSL-D)-catalyzed asymmetric transesterification was performed on gram scale using isopropenyl acetate as an innocuous acyl donor in organic media affording the (S)-alcohol in high enantiomeric excess (>99% ee) and enantiomeric ratio E >150. The lipase (Candida antarctica B, CAL-B)-catalyzed asymmetric hydrolysis of the racemic acetate was performed on gram scale in phosphate buffer affording the (R)-alcohol in high enantiomeric excess (>99% ee) and enantiomeric ratio E >150. The investigation demonstrates that the transesterification of the racemic alcohol in organic solvent was faster than the hydrolysis of the corresponding acetate in phosphate buffer. A GC method was developed to achieve an effective analytical separation of the enantiomers of both substrate and product in one analysis using the chiral stationary phase heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin. |
format |
Article in Journal/Newspaper |
author |
Ghanem, Ashraf Schurig, Volker |
spellingShingle |
Ghanem, Ashraf Schurig, Volker Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol |
author_facet |
Ghanem, Ashraf Schurig, Volker |
author_sort |
Ghanem, Ashraf |
title |
Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol |
title_short |
Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol |
title_full |
Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol |
title_fullStr |
Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol |
title_full_unstemmed |
Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol |
title_sort |
lipase-catalyzed access to enantiomerically pure (r)- and (s)-trans-4-phenyl-3-butene-2-ol |
publishDate |
2003 |
url |
https://researchprofiles.canberra.edu.au/en/publications/e077a474-4d80-4450-92d0-ac8dac8bf6de https://doi.org/10.1016/S0957-4166(02)00745-0 https://researchsystem.canberra.edu.au/ws/files/26895630/Article.pdf http://www.scopus.com/inward/record.url?scp=0037421232&partnerID=8YFLogxK |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Ghanem , A & Schurig , V 2003 , ' Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol ' , Tetrahedron Asymmetry , vol. 14 , no. 1 , pp. 57-62 . https://doi.org/10.1016/S0957-4166(02)00745-0 |
op_rights |
info:eu-repo/semantics/closedAccess |
op_doi |
https://doi.org/10.1016/S0957-4166(02)00745-0 |
container_title |
Tetrahedron: Asymmetry |
container_volume |
14 |
container_issue |
1 |
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57 |
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62 |
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1798836345180782592 |