ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY
The use of biocatalysts in synthetic chemistry is a conventional methodology for preparing enantiomerically enriched compounds. Despite this fact, the number of experiments in chemical teaching laboratories that demonstrate the potential of enzymes in synthetic organic chemistry is limited. We descr...
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ftdoajarticles:oai:doaj.org/article:7a016c00f3a84b25b8fd0256f8675c7c 2023-05-15T13:40:56+02:00 ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY Luís M. R. Solano Nuno M. T. Lourenço 2015-02-01T00:00:00Z https://doi.org/10.5935/0100-4042.20140306 https://doaj.org/article/7a016c00f3a84b25b8fd0256f8675c7c EN ES PT eng spa por Sociedade Brasileira de Química http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015000200285&lng=en&tlng=en https://doaj.org/toc/1678-7064 1678-7064 doi:10.5935/0100-4042.20140306 https://doaj.org/article/7a016c00f3a84b25b8fd0256f8675c7c Química Nova, Vol 38, Iss 2, Pp 285-287 (2015) sec-alcohols esters lípase enantiomers resolution Chemistry QD1-999 article 2015 ftdoajarticles https://doi.org/10.5935/0100-4042.20140306 2022-12-31T05:43:07Z The use of biocatalysts in synthetic chemistry is a conventional methodology for preparing enantiomerically enriched compounds. Despite this fact, the number of experiments in chemical teaching laboratories that demonstrate the potential of enzymes in synthetic organic chemistry is limited. We describe a laboratory experiment in which students synthesized a chiral secondary alcohol that can be used in the preparation of antidepressant drugs. This experiment was conducted by individual students as part of a Drug Synthesis course held at the Pharmacy Faculty, Lisbon University. This laboratory experiment requires six laboratory periods, each lasting four hours. During the first four laboratory periods, students synthesized and characterized a racemic ester using nuclear magnetic resonance spectroscopy and gas chromatography. During the last two laboratory periods, they performed enzymatic hydrolysis resolution of the racemic ester using Candida antarctica lipase B to yield enantiomerically enriched secondary alcohol. Students successfully prepared the racemic ester with a 70%-81% overall yield in three steps. The enzymatic hydrolysis afforded (R)- secondary alcohol with good enantioselectivity (90%-95%) and reasonable yields (10%-19%). In these experiments, students were exposed to theoretical and practical concepts of aromatic acylation, ketone reduction, esterification, and enzymatic hydrolysis. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Química Nova |
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Directory of Open Access Journals: DOAJ Articles |
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English Spanish Portuguese |
topic |
sec-alcohols esters lípase enantiomers resolution Chemistry QD1-999 |
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sec-alcohols esters lípase enantiomers resolution Chemistry QD1-999 Luís M. R. Solano Nuno M. T. Lourenço ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
topic_facet |
sec-alcohols esters lípase enantiomers resolution Chemistry QD1-999 |
description |
The use of biocatalysts in synthetic chemistry is a conventional methodology for preparing enantiomerically enriched compounds. Despite this fact, the number of experiments in chemical teaching laboratories that demonstrate the potential of enzymes in synthetic organic chemistry is limited. We describe a laboratory experiment in which students synthesized a chiral secondary alcohol that can be used in the preparation of antidepressant drugs. This experiment was conducted by individual students as part of a Drug Synthesis course held at the Pharmacy Faculty, Lisbon University. This laboratory experiment requires six laboratory periods, each lasting four hours. During the first four laboratory periods, students synthesized and characterized a racemic ester using nuclear magnetic resonance spectroscopy and gas chromatography. During the last two laboratory periods, they performed enzymatic hydrolysis resolution of the racemic ester using Candida antarctica lipase B to yield enantiomerically enriched secondary alcohol. Students successfully prepared the racemic ester with a 70%-81% overall yield in three steps. The enzymatic hydrolysis afforded (R)- secondary alcohol with good enantioselectivity (90%-95%) and reasonable yields (10%-19%). In these experiments, students were exposed to theoretical and practical concepts of aromatic acylation, ketone reduction, esterification, and enzymatic hydrolysis. |
format |
Article in Journal/Newspaper |
author |
Luís M. R. Solano Nuno M. T. Lourenço |
author_facet |
Luís M. R. Solano Nuno M. T. Lourenço |
author_sort |
Luís M. R. Solano |
title |
ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_short |
ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_full |
ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_fullStr |
ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_full_unstemmed |
ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_sort |
enzymatic resolution of antidepressant drug precursors in an undergraduate laboratory |
publisher |
Sociedade Brasileira de Química |
publishDate |
2015 |
url |
https://doi.org/10.5935/0100-4042.20140306 https://doaj.org/article/7a016c00f3a84b25b8fd0256f8675c7c |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Química Nova, Vol 38, Iss 2, Pp 285-287 (2015) |
op_relation |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015000200285&lng=en&tlng=en https://doaj.org/toc/1678-7064 1678-7064 doi:10.5935/0100-4042.20140306 https://doaj.org/article/7a016c00f3a84b25b8fd0256f8675c7c |
op_doi |
https://doi.org/10.5935/0100-4042.20140306 |
container_title |
Química Nova |
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