A linearized form of cyclic di-AMP
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Parent Compound(s)
17753Cyclic di-AMP (sodium salt)
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5'-pApA (sodium salt)

Item No. 33886

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5′-O-phosphonoadenylyl-(3′→5′)-adenosine, trisodium salt
Synonyms
  • c-di-AMP Control
  • Cyclic di-AMP Negative Control
Molecular Formula
C20H23N10O13P2 • 3Na
Formula Weight
742.4
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Water: soluble
SMILES
O=P(O[C@H]1[C@@H](O)[C@@](N2C3=NC=NC(N)=C3N=C2)([H])O[C@@H]1COP([O-])([O-])=O)([O-])OC[C@@H]4[C@@H](O)[C@@H](O)[C@@](N5C6=NC=NC(N)=C6N=C5)([H])O4.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C20H26N10O13P2.3Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(32)11(31)7(41-19)1-40-45(37,38)43-14-8(2-39-44(34,35)36)42-20(13(14)33)30-6-28-10-16(22)24-4-26-18(10)30;;;/h3-8,11-14,19-20,31-33H,1-2H2,(H,37,38)(H2,21,23,25)(H2,22,24,26)(H2,34,35,36);;;/q;3*+1/p-3/t7-,8-,11-,12-,13-,14-,19-,20-;;;/m1.../s1
InChi Key
FZHMLQPWUIQMMB-JJCYRVQFSA-K
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    700 µg

    $236

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    Product Description

    5'-pApA is a linearized form of cyclic di-AMP, a bacterial second messenger that activates the host innate immune system through stimulator of interferon genes (STING).1,2,3,4 It is a metabolite of cyclic di-AMP (Item No. 17753) formed via hydrolysis by various phosphodiesterases (PDEs).5 5'-pApA is intended for use as a negative control for cyclic di-AMP signaling.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Burdette, D.L., Monroe, K.M., Sotelo-Troha, K., et al. STING is a direct innate immune sensor of cyclic-di-GMP. Nature 478(7370), 515-518 (2011).

    2. Woodward, J.J., Iavarone, A.T., and Portnoy, D.A. c-di-AMP secreted by intracellular Listeria monocytogenes activates a host type I interferon response. Science 328(5986), 1703-1705 (2010).

    3. Witte, C.E., Whiteley, A.T., Burke, T.P., et al. Cyclic di-AMP is critical for Listeria monocytogenes growth, cell wall homeostasis, and establishment of infection. mBio 4(3), e00282-00213 (2013).

    4. Fahmi, T., Port, G.C., and Cho, K.H. c-di-AMP: An essential molecule in the signaling pathways that regulate the viability and virulence of gram-positive bacteria. Genes (Basel) 8(8), 197 (2017).