Synthesis of deuterated vitamin B6 compounds

3-Hydroxy-4-(hydroxymethyl)-5-(hydroxymethyl-d2)-2-methylpyridine (pyridoxine-d2) was prepared by reduction of α4-3-0-isopropylidene-5-pyridoxic acid with lithium aluminum deuteride. Deuterium was inserted in the 2-methyl group using base catalyzed exchange between deuterium oxide and N-benzyl pyridoxine. Pyridoxine-d2 was converted to pyridoxal, pyridoxamine, pyridoxic acid, pyridoxine phosphate, pyridoxal phosphate, and pyridoxamine phosphate. After acetylation the nonphosphorylated forms could be analyzed by gas chromatography-chemical ionization mass spectroscopy. (author)