Nucleic Acid Related Compounds. 5. The Transformation of Formycin and Tubercidin Into 2'- and 3'-Deoxynucleosides,
UTAH UNIV SALT LAKE CITY DEPT OF CHEMISTRY
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Reaction of tubercidin 4-amino-7-beta-D-ribofuranosylpyrrolo2,3-dpyrimidine with alpha-acetoxyisobutyryl chloride in the presence of excess sodium iodide in acetonitrile gave an acylated iodo intermediate which was converted into 3-deoxytubercidin by hydrogenolysis and subsequent saponification. Analogous treatment of formycin 7-amino-3-beta-D-ribofuranosylpyrazolo4,3-dpyrimidine gave 3-deoxyformycin and 2-deoxyformycin in an approximate ratio of 32. These purified nucleosides were individually deaminated enzymatically to give 3-deoxyformycin B and 2-deoxyformycin B. Biological rationale, n.m.r., and mass spectra of these antibiotic-derived deoxynucleosides are discussed.