A nucleoside analog and GMP synthase inhibitor
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Decoyinine

Item No. 13851

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4',5'-didehydro-1'-C-(hydroxymethyl)-adenosine
CAS Number
2004-04-8
Synonyms
  • Angustmycin A
Molecular Formula
C11H13N5O4
Formula Weight
279.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
OC[C@](OC1=C)(N2C(N=CN=C3N)=C3N=C2)[C@@H]([C@@H]1O)O
InChi Code
InChI=1S/C11H13N5O4/c1-5-7(18)8(19)11(2-17,20-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-4,7-8,17-19H,1-2H2,(H2,12,13,14)/t7-,8-,11-/m1/s1
InChi Key
UZSSGAOAYPICBZ-SOCHQFKDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $107

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    5 mg

    $451

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    Product Description

    Decoyinine is a nucleoside analog and a reversible and non-competitive inhibitor of GMP synthase (IC50 = 17.3 µM).1 It reduces intracellular levels of GMP, GDP, and GTP, induces sporulation, and inhibits growth and cell wall synthesis in B. subtilis.2,3,4 It also reverses inhibition of aerial mycelium formation in Streptomyces grown in the presence of excess nutrients.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakamura, J., and Lou, L. Biochemical characterization of human GMP synthetase. The Journal of Biological Chemisty 270(13), 7347-7353 (1995).

    2. Uratani, B., Lopez, J.M., and Freese, E. Effect of decoyinine on peptidoglycan synthesis and turnover in Bacillus subtilis. J. Bacteriol. 154(1), 261-268 (1983).

    3. Zain-ul-abedin, Lopez, J.M., and Freese, E. Induction of bacterial differentiation by adenine- and adenosine-analogs and inhibitors of nucleic acid synthesis. Nucleos. Nucleot. 2(3), 257-274 (1983).

    4. Bai, U., Lewandoski, M., Dubnau, E., et al. Temporal regulation of the Bacillus subtilis early sporulation gene spo0F. J. Bacteriol. 172(9), 5432-5439 (1990).

    5. Ochi, K. A decrease in GTP content is associated with aerial mycelium formation in Streptomyces MA406-A-1. J. Gen. Microbiol. 132(2), 299-305 (1986).