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2002
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In the Laboratory
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Synthesis of a Racemic Ester and Its Lipase–Catalyzed Kinetic Resolution
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Delia Stetca, Isabel W. C. E. Arends, and Ulf Hanefeld
Gebouw voor Scheikunde, Technische Universiteit Delft, Delft, The Netherlands
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November 2002
Vol. 79 No. 11
p. 1351
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| Abstract |
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A first-year organic chemistry laboratory experiment is described in which an enzyme is utilized for the kinetic resolution of a racemic ester. In the first step, the racemic ester is synthesized from racemic 1-phenylethanol and acetic anhydride in the presence of pyridine. In the second step, only one of the two enantiomers of the racemic ester is selectively hydrolyzed. This reaction is enzyme-catalyzed and it clearly demonstrates the great ease with which enzymes can be used for the synthesis of enantiomerically-enriched compounds. The two enantiomerically-enriched compounds formed are isolated and analyzed for their optical purity.
In these experiments the students are exposed to enzyme chemistry in combination with standard organic methods. Indeed, all the products are purified by techniques that are applied in the research laboratory (column chromatography and distillation), ensuring that these experiments come as close to the research environment as possible. By means of these experiments, topics such as enantioselective synthesis, enzymes in synthesis, enzyme kinetics, and analytical techniques such as IR, TLC, and optical rotation can be introduced to the students.
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| Supplement |
Lab handouts for the students and instructor notes are available.
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 Contents |
JCE2002p1351W.doc (Microsoft Word)
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| Download |
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| More Information |
Citation |
Stetca, Delia; Arends, Isabel W. C. E.; Hanefeld, Ulf. J. Chem. Educ. 2002 79 1351.
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Keywords |
Bioorganic Chemistry; Catalysis; Enzymes; Organic Chemistry; Organic Synthesis
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History |
Created:
Last Updated: |
September 30, 2002
March 16, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
2002
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November
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1351
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