Stereochemistry of the Ethanolamine Ammonia Lyase Reaction with Stereospecifically Labeled 1>-2-Aminoethanol

Article abstract of DOI:10.1021/ja00322a037

The antipodes of <1-2H₁>-2-aminoethanol (10) have been synthesized from (S)-<α-2H₁>benzyl alcohol and separately subjected to the action of ethanolamine ammonia lyase in the presence of alcohol dehydrogenase, in order to determine whether the migration of a hydrogen atom from C-1 to C-2 during acetaldehyde formation is stereospecific. (R)-10 reacts 4 times as fast as (S)-10, the isotope effect showing that the pro-S hydrogen migrates preferentially in each case. 1H and 13C NMR spectra of the ethanol formed show that (R)-10 leads to CH3CHDOH while (S)-10 affords DCH2CH2OH, confirming the stereoselectivity of hydrogen transfer.