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Chiral compounds can have unique properties and are becoming increasingly
important in pharmaceutical, chemical and agricultural industries. In this
laboratory exercise, students compare and contrast chemical vs. enzyme-mediated procedures for introducing chirality into a molecule and
gain experience with the principles and experimental techniques used to
prepare and separate enantiomers. Over the course of four, 3-hour lab
periods, students characterize (1) racemic and enantiomerically enriched
products of the sodium borohydride reduction of ethyl acetoacetate with and
without the use of a L-tartaric acid and (2) products obtained with an
enzyme-mediated reduction using Baker's yeast. This exercise provides a
framework for discussing some of the unique challenges associated with using
enzyme-mediated procedures for developing environmentally benign chiral
Supplemental materials are provided on the J. Chem. Educ. website and include instructor notes and student handouts for the laboratory procedure and the chiral GC analysis.
Summary prepared May 2005 by Julie A. Haack, Department of Chemistry at the University of Oregon.
Pohl, N.; Clague, A.; Schwarz, K. J. Chem. Educ., Print 2002, 79, pp 727-728.