Copyright © 1997, 2001 by Galen Daryl Knight and VitaleTherapeutics, Inc.

Alkylation of Vitaletheine's Sulfenic Acid with Phorbol Esters

Although other possible explanations exist for the cancer promoting activities of phorbol esters, the ester groups of these compounds are recognized as being essential for their undesirable activities. The long hydrocarbon chain esterified to phorbol may effectively anchor the otherwise water-soluble, phorbol moiety in the membrane where the monooxygenase is located and where this enzyme is generating sulfenic acids of the vitaletheine modulators; without the ester moieties, phorbol is far less potent as a tumor promoter. Tautomerization to the enol in this phorbol portion provides an effective reagent for removing sulfenic acids of the vitaletheine modulators. This tautomerization probably is not direct, but can occur through a conjugation within the 5-membered ring containing the ketone. The enol tautomer, as in many other toxins, is probably stabilized by the hydroxyl group vicinal to the keto group.


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