Mechanism of action of vitamin K.

We have discovered a novel, spontaneous model oxidation that leads to a powerful base capable of carrying out a carbon-carbon bond forming condensation reaction analogous to that observed in the vitamin K-mediated carboxylation of glutamate. The model sequence incorporates a novel base-strength enhancement sequence and it implicates molecular oxygen as the initiating factor in the vitamin K-dependent carboxylation. When the oxygenation is carried out under an atmosphere of (18)O2, two atoms of (18)O are incorporated into the vitamin K oxide product. Selective (18)O labelling defines the carbonyl group next to methyl as the active site of the vitamin K.