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■ 1-Ethyl-3-methylisoguanosine, a Doridosine Derivative

Yong Hae Kim,* Sang Joa Jee, and Harry S. Mosher

*Department of Applied Chemistry, Korea Advanced Institute of Science and Technology, P.O.Box 150 Chong-Yang-ni, Seoul 131, Korea

Abstract

1-Ethyl-6-imino-3-methyl-2-oxo-9-β-D-ribofuranosylpurine (2, 1-ethyl-3-methyl-isoguanosine) has been synthesized from 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carbonitrile. This modified purine, by virtue of substituents on both N¹ and N³ nitrogens is frozen in the 6-imino form; its uv spectrum is compared to that of analogs which can exist in the tautomeric 6-amino ⇔ 6-imino forms. It is relatively stable to hydrolysis of the 9-ribosyl bond in contrast to other N³-substituted nucleosides.