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2000
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In the Laboratory
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Probing the Active Site of Yeast Alcohol Dehydrogenase through Microscale Yeast-Mediated Reductions of Acetophenone and Acetylpyridines. A Collaborative and Research-Based Advanced Bioorganic Chemistry Laboratory Project
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Moses Lee, Jennifer Azbell, Michael Carnahan, Kari Cox,
Joey Espinosa, Ray Feaster, Robert Hirsch, Andrew Lam,
Shane Roller, Brent Steadman, and James Toth
Department of Chemistry, Furman University, Greenville, SC 29613-1120
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March 2000
Vol. 77 No. 3
p. 363
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| Abstract |
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A collaborative and research-oriented advanced bioorganic chemistry project that probed the
structure and reactivity relationship of yeast alcohol dehydrogenase (YADH) is reported. The
project involved microscale and stereoselective reductions of acetophenone and 2-, 3-, and
4-acetylpyridines by yeast. Each pair of students was assigned two substrates to ensure
duplication of each individual experiment, and the results were combined. At the end of the
project, each student had to prepare a detailed report based on the entire set of results.
The acetylpyridines being better substrates than acetophenone was consistent with the polar
nature of the active site of YADH. The major enantiomer of the optically active secondary
alcohols was (S) in all cases, and that was also consistent with the transfer of a hydride ion
from NADH to the re-face of the prochiral carbonyl group. The results showed 4-acetylpyridine
to be the best substrate for product formation and asymmetric induction. This observation is
presumably a result of favorable hydrogen bonding interactions between the pyridyl-N atom and
the hydroxy group of Tyr-140 in the substrate binding site of the enzyme.
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| Supplement |
An Outline for the Laboratory Exercise, experimental procedures, potential
hazards, Tips for Success, and NMR spectra are included.
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 Contents |
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| More Information |
Citation |
Lee, Moses; Azbell, Jennifer; Carnahan, Michael; Cox, Kari; Espinosa, Joey; Feaster, Ray; Hirsch, Robert; Lam, Andrew; Roller, Shane; Steadman, Brent; Toth, James. J. Chem. Educ. 2000 77 363.
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Keywords |
Biochemistry; Bioorganic Chemistry; Enzymes; Inquiry-Based / Discovery Method; Microscale; Molecular Recognition
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History |
Created:
Last Updated: |
February 14, 2000
August 31, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
2000
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March
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363
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