Abstract
Summary An electrochemical synthesis of isomer-free 6-methylpterin from folic acid has been developed. Folic acid is reduced to 7,8-dihydrofolic acid via 5,8-dihydrofolic acid. Under acidic conditions the C(9)-N(10) bond in 7,8-dihydrofolic acid is reduced electrochemically, resulting in 6-methyl-7,8-dihydropterin and p -aminobenzoylglutamic acid. 6-Methylpterin can be obtained by oxidation of the corresponding dihydropterin. 7,8-Dihydrofolic acid is stable under anaerobic conditions between pH 4 and 9. Under strongly acidic conditions hydrolysis of the C(9)-N(10) bond takes place and 6-hydroxymethyl-7,8-dihydropterin and p -aminobenzoylglutamic acid are obtained. Under aerobic conditions oxidative cleavage of the C(9)-N(10) bond results in various pterin derivatives. Some 6-azomethinpterins were synthesized. Voltammetric studies studies of these compounds show that the reduction of the pterin nucleus follows the same general pathway described for the reduction of pterins. Reduction of the C(9)-N(10) double bond proceeds through a reversible two-electron step, followed by a transformation, resulting in saturation of the bond.
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