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Decoyinine

BVT-0030-M001 1 mg INQ
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Additional Information

Product Data
Synonyms Angustmycin A; U-7984; 9-(6-Deoxy-D-β-erythro-hex-5-en-2-ulofuranosyl)-adenine
Properties
Formula C11H13N5O4
MW 279.3
CAS 2004-04-8
RTECS AU6256000
Source/Host Isolated from Streptomyces sp. S 2113.
Purity ≥98% (NMR)
Appearance White to off-white solid.
Solubility Soluble in DMSO (warm), water or 100% ethanol: poorly soluble in methanol.
Identity Determined by 1H-NMR.
Origin Manufactured by BioViotica.
InChi Key UZSSGAOAYPICBZ-SOCHQFKDSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light when in solution.
Use/Stability Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.
Documents
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Product Description

  • Nucleoside antibiotic.
  • Antitumor compound.
  • Xanthosine monophosphate (XMP) aminase inhibitor.
  • RNA synthesis inhibitor.
  • Specific GMP synthase inhibitor.
  • Reduces intracellular GTP levels.

Product References

  1. Studies on a new antibiotic, angustmycin: H. Sakai, et al.; J. Antibiot. 7, 116 (1954)
  2. Studies on a new antibiotic, angustmycin. I: H. Yuntsen, et al.; J. Antibiot. 7, 113 (1954)
  3. Studies on angustmycin. III: H. Yuntsen, et al.; J. Antibiot. 9, 195 (1956)
  4. On the studies of angustmycins. VI. Chemical structure of angustmycin A: H. Yuntsen; J. Antibiot. 11, 79 (1958)
  5. Purine nucleosides. XXII. The synthesis of angustmycin A (decoyinine) and related unsaturated nucleosides: J.R. McCarthy, Jr., et al.; J. Am. Chem. Soc. 90, 4993 (1968)
  6. Effects of several tumor-inhibitory antibiotics on immunological responses: H. Yamaki, et al.; J. Antibiot. 22, 315 (1969)
  7. Halo sugar nucleosides. 5. Synthesis of angustmycin A and some base analogues: E.J. Prisbe, et al.; J. Org. Chem. 41, 1836 (1976)
  8. A decrease in GTP content is associated with aerial mycelium formation in Streptomyces MA406-A-1: K. Ochi; J. Gen. Microbiol. 132, 299 (1986)
  9. Extracellular control of spore formation in Bacillus subtilis: A.D. Grossman & R. Losick; PNAS 85, 4369 (1988)
  10. Nucleoside antibiotics: structure, biological activity, and biosynthesis: K. Isono; J. Antibiot. 41, 1711 (1988)
  11. A target for carbon source-dependent negative regulation of the citB promoter of Bacillus subtilis: A. Fouret & A.L. Sonenshein; J. Bacteriol. 172, 835 (1990)
  12. Sporulation of Streptomyces venezuelae in submerged cultures: M.A. Glazebrook, et al.; J. Gen. Microbiol. 136, 581 (1990)
  13. Conformational studies on some Cl'-branched beta-D-nucleosides by 1H-NMR spectroscopy and molecular mechanics calculations: J. Plavec, et al.; J. Biochem. Biophys. Meth. 26, 317 (1993)
  14. Biochemical characterization of human GMP synthetase: J. Nakamura & L. Lou; J. Biol. Chem. 270, 7347 (1995)
  15. Guanine nucleotides guanosine 5'-diphosphate 3'-diphosphate and GTP co-operatively regulate the production of an antibiotic bacilysin in Bacillus subtilis: T. Inaoka, et al.; J. Biol. Chem. 278, 2169 (2003)
  16. Expression of kinA and kinB of Bacillus subtilis, necessary for sporulation initiation, is under positive stringent transcription control: S. Tojo, et al.; J. Bacteriol. 195, 1656 (2013)
  17. Pharmacological targeting of guanosine monophosphate synthase suppresses melanoma cell invasion and tumorigenicity: A. Bianchi-Smiraglia, et al.; Cell Death Differ. 22, 1858 (2015)
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