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Synfacts 2010(8): 0861-0861  
DOI: 10.1055/s-0030-1257745
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (S)-Profens

Contributor(s): Philip Kocienski
J. A. Friest, Y. Maezato, S. Broussy, P. Blum*, D. B. Berkowitz*
University of Nebraska, Lincoln, USA
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Recombinant alcohol dehydrogenase-10 from the hyperthermophile Solfolobus solfataricus (SsADH-10) effects efficient dynamic reductive kinetic resolution of 2-arylpropanals. The reaction is performed at 80 ˚C using NADH as the catalytic reductant and 5% EtOH as the stoichiometric reductant. Success depends on the rapid equilibration of the 2-arylpropanal substrates (e.g. A) under the basic reaction conditions (pH 9). Only one of twelve substrates examined failed to react. The yields ranged from 55-99% and the er was generally >95:5.