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  Home > JCE Print > Journal of Chemical Education > Issues > 1996  > May  >
Laboratory Experiments
Chemoenzymatic Synthesis of an Enantiomerically Pure Lactone: A Three-Step Synthesis for Undergraduate Organic Chemistry Laboratory
Cynthia K. McClure
Montana State University, Bozeman, MT 59717

H. Keith Chenault
University of Delaware, Newark, DE 19716

Cover
May 1996
Vol. 73 No. 5
p. 467
Abstract
A three-step laboratory sequence for the undergraduate organic laboratory is described. This series of experiments requires a student to use the product from one reaction as the starting material for a subsequent reaction, and thus the affords the student a "real world" experience of multistep synthesis. Thermal extrusion of sulfur dioxide from sulfolene is used to generate 1,3-butadiene in situ for a Diels-Alder cyclization with maleic anhydride. The anhydride is then reduced to the diol with lithium aluminum hydride. Oxidation of the diol to the chiral lactone is catalyzed by horse-liver alcohol dehydrogenase. This enzymatic oxidation illustrates in situ cofactor regeneration and allows students to measure simple enzyme kinetics.
More Information
*  Citation
 McClure, Cynthia K.; Chenault, H. Keith. J. Chem. Educ. 1996 73 467.
*  Keywords
*  History
 Created:
Last Updated:		 9/23/1999
5/22/2006
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