STEREOSELECTIVE BENZYLIC DEPROTONATION IN THE ENZYMATIC REARRANGEMENTOF N-ACETYLDOPAMINE DERIVED O-QUINONE TO THE P-QUINONE METHIDE

Authors
PETER MG MERZ A
Citation
Mg. Peter et A. Merz, STEREOSELECTIVE BENZYLIC DEPROTONATION IN THE ENZYMATIC REARRANGEMENTOF N-ACETYLDOPAMINE DERIVED O-QUINONE TO THE P-QUINONE METHIDE, Tetrahedron : asymmetry, 6(4), 1995, pp. 839-842
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
4
Year of publication
1995
Pages
839 - 842
Database
ISI
SICI code
0957-4166(1995)6:4<839:SBDITE>2.0.ZU;2-M
Abstract
(R)-N-acetyl-[beta-H-2(1)]-dopamine {(R)-1} undergoes an enzyme cataly zed oxidative tautomerization to quinone methide 3 with loss of the be nzylic H-Si, as proven by isolation of deuteriated rac. N-acetylnoradr enaline (4), while (S)-[beta-H-2(1)]-1 loses the deuterium label. Thus , the o-quinone-p-quinone methide isomerization is a stereoselective e nzymatic reaction.