Nucleic Acid Related Compounds. 5. The Transformation of Formycin and Tubercidin into 2′- and 3′-Deoxynucleosides
Reaction of tubercidin (4-amino-7-β-D-ribofuranosylpyrrolo[2,3-d]pyrimidine) (1) with α-acetoxyisobutyryl chloride in the presence of excess sodium iodide in acetonitrile gave an acylated iodo intermediate (2) which was converted into 3′-deoxytubercidin (4) by hydrogenolysis and subsequent saponification.Analogous treatment of formycin (7-amino-3-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine) (5) gave 3′-deoxyformycin (6) and 2′-deoxyformycin (7) in an approximate ratio of 3:2. These purified nucleosides, 6 and 7 were individually deaminated enzymatically to give 3′-deoxyformycin B (8) and 2′-deoxyformycin B(9).Biological rationale, n.m.r., and mass spectra of these antibiotic-derived deoxynucleosides are discussed.
1967 ◽
Vol 89
(11)
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pp. 2719-2725
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1989 ◽
Vol 62
(11)
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pp. 3750-3751
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1951 ◽
Vol 189
(1)
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pp. 151-157
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1971 ◽
Vol 8
(2)
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pp. 225-230
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Keyword(s):
1983 ◽
Vol 26
(5)
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pp. 661-666
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1968 ◽
Vol 89
(6)
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pp. 594-596
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