Stereoselective Benzylic Deprotonation in the Enzymatic Rearrangement of N-Acetyldopamine Derived o-Quinone to the p-Quinone Methide

Article abstract of DOI:10.1016/0957-4166(95)00083-2

(R)-N-acetyl-<β-²H₁>-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-²H₁>-1 loses the deuterium label.Thus, the o-quinone-p-quinone methide isomerization is a stereoselective enzymatic reaction.