Educação doi number 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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ftciteseerx:oai:CiteSeerX.psu:10.1.1.1079.5431 2023-05-15T13:37:29+02:00 Educação doi number ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY Luís M R Solano Nuno M T Lourenço The Pennsylvania State University CiteSeerX Archives application/pdf http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1079.5431 http://www.quimicanova.sbq.org.br/imagebank/pdf/ED20140104.pdf en eng http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1079.5431 http://www.quimicanova.sbq.org.br/imagebank/pdf/ED20140104.pdf Metadata may be used without restrictions as long as the oai identifier remains attached to it. http://www.quimicanova.sbq.org.br/imagebank/pdf/ED20140104.pdf text ftciteseerx 2020-05-03T00:20:31Z 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. Text Antarc* Antarctica Unknown |
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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. |
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The Pennsylvania State University CiteSeerX Archives |
format |
Text |
author |
Luís M R Solano Nuno M T Lourenço |
spellingShingle |
Luís M R Solano Nuno M T Lourenço Educação doi number ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
author_facet |
Luís M R Solano Nuno M T Lourenço |
author_sort |
Luís M R Solano |
title |
Educação doi number ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_short |
Educação doi number ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_full |
Educação doi number ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_fullStr |
Educação doi number ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_full_unstemmed |
Educação doi number ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY |
title_sort |
educação doi number enzymatic resolution of antidepressant drug precursors in an undergraduate laboratory |
url |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1079.5431 http://www.quimicanova.sbq.org.br/imagebank/pdf/ED20140104.pdf |
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Antarc* Antarctica |
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Antarc* Antarctica |
op_source |
http://www.quimicanova.sbq.org.br/imagebank/pdf/ED20140104.pdf |
op_relation |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1079.5431 http://www.quimicanova.sbq.org.br/imagebank/pdf/ED20140104.pdf |
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