Accession Number:

AD0770809

Title:

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

Descriptive Note:

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:

1972-11-07

Pagination or Media Count:

10.0

Abstract:

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.

Descriptors:

• *Nucleosides
• *Antibiotics
• Chemical reactions
• Nuclear magnetic resonance
• Mass spectra

Subject Categories:

• Biochemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE