ORGN 772 |
| Previous reports have established that chiral sulfoxides can inhibit horse liver alcohol dehydrogenase (HLADH) oxidation of ethanol with greater efficiency when using the (S)-enantiomer. HLADH is a NAD dependent enzyme and therefore the rate of the enzymatic oxidation can be conveniently monitored by observing the formation of NADH at 340 nm. (S)-Methyl p-tolyl sulfoxide produced an IC50 value against HLADH of 40 µM, while the (R)-enantiomer was 970 µM. A series of enzyme-catalyzed oxidations of ethanol were conducted at constant methyl p-tolyl sulfoxide concentration, but at variable stereochemical composition of the sulfoxide, 100% (R) to 100% (S). The rate of NADH formation was found to decrease linearly as the enantiomeric excess of the (S)-enantiomer increased. The %ee of many sulfoxide samples of unknown stereochemical composition can be analyzed in a high-throughput manner. |
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Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |