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  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > June  >
In the Laboratory
Multi-Choice Enzymatic Resolutions of Racemic Secondary Alcohols Using Candida antarctica Lipase B. A Collaborative Experiment for Advanced Undergraduates
Francisca Rebolledo and Ramón Liz
Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, E-33071 Oviedo, Spain
Cover
June 2005
Vol. 82 No. 6
p. 930
Abstract
An advanced bioorganic chemistry laboratory set of experiments is described in which the lipase B from Candida antarctica is used for the kinetic resolution of four racemic secondary alcohols. The biotransformations are transesterification reactions of these alcohols, as well as hydrolyses and aminolyses of (±)-1-phenylethyl acetate. Independent work is assigned to each student, and the overall results are analyzed at the end of the laboratory course. Mosher’s method and the so-called modified Mosher’s method are used to determine the enantiomeric excesses and absolute configurations, respectively, of products and remaining substrates. In addition to learning several advanced laboratory techniques and making intensive use of NMR spectroscopy, the students become familiar with enzymatic methodologies and, especially, with the employment of enantioselectivity values for evaluating the stereochemical efficiency of the processes.
Supplement
Instructions for the students and notes for the instructor are available.
*  Contents JCE2005p0930W.doc (Microsoft Word)
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*  Citation
 Rebolledo, Francisca; Liz, Ramón. J. Chem. Educ. 2005 82 930.
*  Keywords
 Bioorganic Chemistry; Catalysis; Chromatography; Enzymes; Hands-On Learning / Manipulatives; Laboratory Instruction; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Stereochemistry; Upper-Division Undergraduate
*  History
 Created:
Last Updated:		 April 27, 2005
May 6, 2005
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