ELECTROCHEMICAL REDUCTION OF PURINE, ADENINE AND RELATED COMPOUNDS POLAROGRAPHY AND MACROSCALE ELECTROLYSIS. Report No. 62
The electrochemical reduction of purine and certain derivatives was examined polarographically, coulometrically, and by macroscale reduction over the normal pH range. The reduction prcducts were investigated spectrophotometrically and chemically as well as polarographically. Purine is reduced in two 2e stages: the first stage involved reduction of the 1,6 double bond to 1,6-dihydropurine; the second stage involves further reduction to 1,2,3,6-tetrahydropurine which then hydrolyzes to a 4-aminoimidazole. The product of the first purine 2e reduction is slowly oxidized in the presence of oxygen to regenerate purine. Adenine (6-aminopurine) undergoes a single 6e reduction, which involves a 2e hydrogenation of the 1,6 double bond, followed by the 2e reduction of the 2,3 double bond, deamination at the 6-position, further 2e reduction of the regenerated 1,6 double bond, and hydrolytic cleavage at the 2,3 position to give the same product as in the over-all 4e purine reduction. Under polarographic conditions the deamination of adenine is negligible, resulting in a 4e wave. Hypoxanthine (6-hydroxypurine) apparently only undergoes a 2e reduction to 2,3- dihydrohypoxanthine, which then hydrolyzes. 2-Hydroxypurine is postulated to be reduced at about the same potential as purine itself. Adenine and the completely reduced forms of it and of purine lower the overpotential of hydrogen ion reduction. (auth)
- Research Organization:
- Michigan. Univ., Ann Arbor
- NSA Number:
- NSA-15-029164
- OSTI ID:
- 4840920
- Report Number(s):
- TID-13497
- Country of Publication:
- United States
- Language:
- English
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