Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate 1H NMR Experiment To Introduce Chiral Chemistry

• Juan A. Faraldos ^[3] ; José-Luis Giner ^[3] ; David H. Smith ^[1] ; Mark Wilson ^[1] ; Kyla Ronhovde ^[1] ; Erin Wilson ^[1] ; David Clevette ^[1] ; Andrea E. Holmes ^[1] ; Kerry Rouhier ^[2]
  1. [1] Doane College

     Doane College

     City of Crete, Estados Unidos

     
  2. [2] Kenyon College

     Kenyon College

     Township of College, Estados Unidos

     
  3. [3] Department of Chemistry, SUNY-ESF, Estados Unidos

  Mostrar afiliaciones +
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 88, Nº 3, 2011, págs. 334-336
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • This organic laboratory experiment introduces students to stereoselective enzyme reactions, resolution of enantiomers, and NMR analysis of diastereomers. The reaction between racemic 1-phenylethanol and vinyl acetate in hexane to form an ester is catalyzed by acylase I. The unreacted alcohol is then treated with a chiral acid and the resulting ester diastereomer is analyzed by NMR. This experiment is suitable for group work in the laboratory as several diastereomers are synthesized and compared to determine which enantiomer of 1-phenylethanol reacts with the enzyme.