Structure of ascorbic acid and its biological function: V. Transport of ascorbate and isoascorbate across artificial...

It could be shown by the reduction of the spin label (1,14) located within DPPC vesicles, that Na-ascorbate and K-isoascorbate can permeate membranes. At physiologic pH value, these two compounds exist as electroneutral radicals with a cyclic side chain structure. Ascorbic acid and isoascorbic acid, on the contrary, can hardly permeate such an artificial membrane. Since the radical will cause lipid peroxidation, it must be modified prior to permeation. This can be done by GSH which changes the radical state but maintains the electroneutral bicyclic configuration.