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Oxidizing Action of Purine N-Oxide Esters¹

Memorial Sloan-Kettering Cancer Center, New York, New York 10021

A technique involving O-acetylation of purine N-oxide derivatives in buffered aqueous solutions has permitted studies of the reactivity of many compounds for which the O-acetyl derivatives are not otherwise available. The oxidizing properties of a variety of N-acetoxypurines have been measured through their ability to oxidize iodide ion to iodine, a reaction which is representative of a more general oxidizing ability. Those esters that oxidize iodide ion also catalyze the autoxidation of sulfite, a property characteristic of radicals. The same esters also oxidize cysteine to cysteic acid and tryptophan, tyrosine, and uric acid to yet uncharacterized products. Their oxidizing reactivity was compared with the ability of the same esters to react as electrophiles in another assay that measured the rate of formation of pyridine substitution products. The sulfate ester of 3-hydroxyxanthine has been synthesized. Its reactivity is qualitatively the same as that of 3-acetoxyxanthine but proceeds at a higher rate. Syntheses of S-(8-xanthyl)-N-acetylcysteine, 8-(2-hydroxyethylthio)xanthine, and 1-methyl-8-methylmercaptoguanine are also described.

¹ This investigation was supported in part by National Cancer Institute Grant CA 15274 and American Cancer Society Grant BC 32. This is Paper 59 in a series on "Purine N-Oxides;" No. 58 is Ref. 14.

² David A. Gimbel Memorial Fellow. Present address: Tevi-Assia Pharmaceutical Co., Jerusalem, Israel.

Received 7/10/74. Accepted 9/12/74.