2'-deoxycoformycin: biosynthesis and enzymatic conversion of 8-ketodeoxycoformycin to 2'-deoxycoformycin by streptomyces antibioticus
Adenosine, but not guanosine nor inosine, contributes 10 of the 11 carbons in the biosynthesis of 2'-deoxycoformycin (dCF). /sup 13/C-NMR experiments of the dCF isolated from cultures of S. antibioticus to which (1-/sup 13/C)D-ribose was added, showed that C-1 of ribose serves as the one-carbon precursor for the -CH/sub 2/- (i.e., C-7 of dCF) by insertion between N-1 and C-6 of the purine ring. Tetrahydrofolate is not a one-carbon carrier for C-7 of dCF. Ribose may be converted to PRPP which is then covalently linked at N-1 of the adenine ring (presumably ATP) similar to histidine biosynthesis. 8-KetodCF, one of the postulated intermediates in the biosynthesis of dCF, is converted to dCF in 25% yields by the enzyme, 8-ketodCF dehydrogenase. The enzyme requires NADPH and removes only the proS hydrogen. The reduction of 8-ketodCF proceeds such that the 8-hydroxyl of dCF has the R configuration. ATP is not required. 8-Ketocoformycin is also reduced enzymatically to coformycin.
- Research Organization:
- Temple Univ., School of Medicine, Philadelphia, PA
- OSTI ID:
- 6936826
- Report Number(s):
- CONF-8606151-
- Journal Information:
- Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States), Journal Name: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States) Vol. 45:6; ISSN FEPRA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
550600 -- Medicine
59 BASIC BIOLOGICAL SCIENCES
62 RADIOLOGY AND NUCLEAR MEDICINE
ANTI-INFECTIVE AGENTS
ANTIBIOTICS
BACTERIA
BIOSYNTHESIS
CARBON 13
CARBON ISOTOPES
DRUGS
EVEN-ODD NUCLEI
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
MICROORGANISMS
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEI
RESONANCE
SPECTRA
STABLE ISOTOPES
STREPTOMYCES
SYNTHESIS