Nonenzymatic transformations of enzymatically generated N-acetyldopamine quinone and isomeric dihydrocaffeiyl methyl amide quinone

FEBS Letters
M SugumaranS J Saul

Abstract

We have recently demonstrated that the side chain hydroxylation of N-acetyldopamine and related compounds observed in several insects is caused by a two-enzyme system catalyzing the initial oxidation of catecholamine derivatives and subsequent isomerization of the resultant quinones to isomeric quinone methides, which undergo rapid nonenzymatic hydration to yield the observed products [Saul, S.J. and Sugumaran, M. (1989) FEBS Lett. 249, 155-158]. During our studies on o-quinone/p-quinone methide tautomerase, we observed that quinone methides are also produced nonenzymatically slowly, under physiological conditions. The quinone methide derived from N-acetyldopamine was hydrated to yield N-acetylnorepinephrine as the stable product as originally shown by Senoh and Witkop [(1959) J. Am. Chem. Soc. 81, 6222-6231], while the isomeric quinone methide from dihydrocaffeiyl methylamide exhibited a new reaction to form caffeiyl amide as the stable product. The identity of this product was established by UV and IR spectral studies and by chemical synthesis. We could not find any evidence of intramolecular cyclization of N-acetyldopamine quinone to iminochrome-type compound(s). The importance of quinone methides in these reactions is discu...Continue Reading

Citations

Jan 1, 1990·Archives of Insect Biochemistry and Physiology·M SugumaranH Dali
Jan 1, 1991·Archives of Insect Biochemistry and Physiology·M SugumaranK Nellaiappan
Feb 1, 1993·Chemico-biological Interactions·D C ThompsonP Moldéus
Feb 23, 2011·Marine Drugs·Manickam Sugumaran, William E Robinson
Sep 23, 2016·International Journal of Molecular Sciences·Manickam Sugumaran
Jan 1, 1995·Archives of Insect Biochemistry and Physiology·M Sugumaran, D Ricketts

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