Abstract
( R)- N-acetyl-[ β- 2H 1]-dopamine (R)- 1 undergoes an enzyme catalyzed oxidative tautomerization to quinone methide 3 with loss of the benzylic H Si , as proven by isolation of deuteriated rac. N-acetylnoradrenaline ( 4), while (S)-[β- 2 H 1]- 1 loses the deuterium label. Thus, the o-quinone- p-quinone methide isomerization is a stereoselective enzymatic reaction.
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