Electrochemical behaviour of pyridinoline, a crosslinking amino acid of collagen

Pyridinoline is a crosslinking amino acid isolated from collagen. Polarographic oxidation and reduction potentials of pyridinoline were measured and compared with those of structurally related compounds, 3-hydroxypyridine, pyridoxine, pyridoxal, and N-methylpyridoxine. Oxidation and reduction potentials of these compounds were found to be near anodic and cathodic limit potentials, respectively, except for pyridoxal. This indicates that a 3-hydroxypyridine ring is very difficult to be reduced or oxidized. The reducibility of pyridinoline with a reducing agent, sodium borohydride, was also studied. It was not reduced by the reagent, however, it was found to be decomposed by light during the treatment. These results indicate that pyridinoline is a so-called "non-reducible" crosslink.