Accession Number : AD0770809

Title :   Nucleic Acid Related Compounds. 5. The Transformation of Formycin and Tubercidin Into 2'- and 3'-Deoxynucleosides,

Corporate Author : UTAH UNIV SALT LAKE CITY DEPT OF CHEMISTRY

Personal Author(s) : Robins,Morris J. ; McCarthy,James R. , Jr. ; Jones,Roger A. ; Mengel,Rudolf

Report Date : 07 NOV 1972

Pagination or Media Count : 10

Abstract : Reaction of tubercidin (4-amino-7-beta-D-ribofuranosylpyrrolo(2,3-d)pyrimidine) 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-ribofuranosylpyrazolo(4,3-d)pyrimidine) gave 3'-deoxyformycin and 2'-deoxyformycin in an approximate ratio of 3:2. 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.

Descriptors :   *Nucleosides, *Antibiotics, Chemical reactions, Nuclear magnetic resonance, Mass spectra

Subject Categories : Biochemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE