The enzymatic resolution of enantiomers and the formation of diastereomers: An undergraduate NMR experiment

CHED 1525

David H Smith, david.smith@doane.edu, Department of Chemistry, Doane College, 1014 Boswell Ave, Crete, NE 68333, Jose-Luis Giner, Department of Chemistry, SUNY-ESF, Syracuse, NY 13210, and Juan A. Faraldos, Department of Chemistry, SUNY-ESF, Syracuse, 307 Stadium Place, Syracuse, NY 13210.
This experiment introduces students to stereoselective enzyme reactions, the resolution of enantiomers, the NMR of diastereomers, and even Green Chemistry. Racemic 1-phenylethanol is reacted with acylase in hexane. The unreacted alcohol is then treated with a chiral acid and the resulting diastereomer analyzed by NMR. This relatively inexpensive experiment is especially suitable for group work in the laboratory as several related diastereomers need to be made in order to decide which enantiomer of 1-phenylethanol reacted with the enzyme.
 

Teaching Stereochemistry in the Undergraduate Curriculum
8:30 AM-11:05 AM, Wednesday, April 9, 2008 Hilton New Orleans Riverside -- HEC C, Oral

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008