The reduced (naphthohydroquinone) form of vitamin K is the form of the vitamin involved in vitamin K dependent carboxylation of a range of important proteins.  During the course of the carboxylation, it is oxidized to vitamin K 2,3-epoxide by molecular oxygen, and it is coupling with this oxidation that permits the endergonic carboxylation to occur.  The epoxide is reduced to the active form of the vitamin by the enzyme VKORC1 (the second enzyme in the vitamin K cycle), which is inhibited by the oral anticoagulant, warfarin.  We have discovered a class of simple bridged naphthohydroquinone acetates that function as both adjuvants and inhibitors of warfarin anticoagulation in rats.  In order to understand this activity, we have undertaken hydrolysis and oxidation studies on these compounds and their analogues in order to obtain a better understanding of the chemistry in vivo.

Hydrolysis and redox reactions of methano-bridged analogs of dihydrovitamin K

244th National Meeting (2012)

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