Journal of the American Chemical Society p. 2961 - 2964 (1984)
Update date:2022-08-04
Topics:
Yan, Shou-Jen
McKinnie, B. Gary
Abacherli, Claudio
Hill, Richard K.
Babior, Bernard M.
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.
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