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Synthesis of a Racemic Ester and Its Lipase-Catalyzed Kinetic Resolution
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Abstract
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.
Keywords (Audience):
First-Year Undergraduate / GeneralKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Bioinorganic ChemistryCiting Articles
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate 1H NMR Experiment To Introduce Chiral Chemistry
Juan A. Faraldos and José-Luis Giner , David H. Smith, Mark Wilson, Kyla Ronhovde, Erin Wilson, David Clevette, and Andrea E. Holmes , Kerry RouhierJournal of Chemical Education2011 88 (3), 334-336Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate 1H NMR Experiment To Introduce Chiral Chemistry
Juan A. Faraldos and José-Luis Giner , David H. Smith, Mark Wilson, Kyla Ronhovde, Erin Wilson, David Clevette, and Andrea E. Holmes , Kerry RouhierJournal of Chemical Education2011 88 (3), 334-336This organic laboratory experiment introduces students to stereoselective enzyme reactions, resolution of enantiomers, and NMR analysis of diastereomers. The reaction between racemic 1-phenylethanol and vinyl acetate in hexane to form an ester is ...
Enzymatic Resolution and Separation of Secondary Alcohols Based on Fatty Esters as Acylating Agents
Carlos M. Monteiro and Carlos A. M. Afonso, Nuno M. T. LourençoJournal of Chemical Education2010 87 (4), 423-425Enzymatic Resolution and Separation of Secondary Alcohols Based on Fatty Esters as Acylating Agents
Carlos M. Monteiro and Carlos A. M. Afonso, Nuno M. T. LourençoJournal of Chemical Education2010 87 (4), 423-425The enzymatic resolution of rac-1-phenylethanol using ethyl myristate as acylating agent and solvent and Candida antarctica lipase B (CAL-B) as biocatalyst was demonstrated with catalyst and medium reuse. Both enantiomers of 1-phenylethanol were isolated ...
The Finkelstein Reaction: Quantitative Reaction Kinetics of an SN2 Reaction Using Nonaqueous Conductivity
R. David Pace and Yagya RegmiJournal of Chemical Education2006 83 (9), 1344The Finkelstein Reaction: Quantitative Reaction Kinetics of an SN2 Reaction Using Nonaqueous Conductivity
R. David Pace and Yagya RegmiJournal of Chemical Education2006 83 (9), 1344Two essential concepts for students to grasp in the undergraduate organic chemistry sequence are substitution chemistry and elimination chemistry (SN1/SN2 and E1/E2). However, students are often confounded by the seemingly endless series of structure–...
4-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison
Annemieke W. C. van den Berg and Ulf HanefeldJournal of Chemical Education2006 83 (2), 2924-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison
Annemieke W. C. van den Berg and Ulf HanefeldJournal of Chemical Education2006 83 (2), 292The synthesis of esters is an essential part of first- and second-year organic chemistry laboratory classes. To highlight the differences between two standard approaches towards esters, a set of experiments was developed. With these experiments the ...
Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands
Albrecht Mannschreck and Roland KiesswetterJournal of Chemical Education2005 82 (7), 1034Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands
Albrecht Mannschreck and Roland KiesswetterJournal of Chemical Education2005 82 (7), 1034The intermolecular interactions of one enantiomer with a chiral auxiliary molecule and the interactions of the other enantiomer with the auxiliary are considered. Different functions of the latter give rise to the following well-known aspects of organic ...
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- Received: August 03, 2009
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