A bacterial second messenger
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Metabolite(s)
338865'-pApA (sodium salt)
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Cyclic di-AMP (sodium salt)

Item No. 17753

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
adenylyl-(3'→5')-3'-adenylic acid, cyclic nucleotide, disodium salt
CAS Number
2734909-87-4
Synonyms
  • c-di-AMP
  • Cyclic di-Adenosine monophosphate
  • 3',5'-Cyclic diadenylic acid
  • Cyclic diadenylate
Molecular Formula
C20H22N10O12P2 • 2Na
Formula Weight
702.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
λmax
205, 260 nm
SMILES
NC1=NC=NC2=C1N=CN2[C@H](O3)[C@H](O)[C@@](OP(OC[C@@]4([H])O[C@@H](N5C(N=CN=C6N)=C6N=C5)[C@H](O)[C@@]([H])4O7)([O-])=O)([H])[C@@]3([H])COP7([O-])=O.[Na+].[Na+]
InChi Code
InChI=1S/C20H24N10O12P2.2Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30;;/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26);;/q;2*+1/p-2/t7-,8-,11-,12-,13-,14-,19-,20-;;/m1../s1
InChi Key
IXWPEIRAKLMJQW-VEQUCWRQSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    Cyclic di-AMP (c-di-AMP) is a second messenger produced by bacteria but not by mammals. Generated by a family of diadenylate cyclases, c-di-AMP can impact bacterial cell growth, cell wall homeostasis, pathogenicity, and other cellular functions.1,2,3 Bacteria-derived cyclic dinucleotides, including c-di-AMP, trigger the expression of interferon genes in mammalian cells.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schaap, P. Cyclic di-nucleotide signaling enters the eukaryote domain. IUBMB Life 65(11), 897-903 (2013).

    2. Luo, Y., and Helmann, J.D. Analysis of the role of Bacillus subtilis σM in β-lactam resistance reveals an essential role for c-di-AMP in peptidoglycan homeostasis. Mol. Microbiol. 83(3), 623-639 (2012).

    3. Corrigan, R.M., and Gründling, A. Cyclic di-AMP: Another second messenger enters the fray. Nat. Rev. Microbiol. 11, 513-524 (2013).

    4. Konno, H., Konno, K., and Barber, G.N. Cyclic dinucleotides trigger ULK1 (ATG1) phosphorylation of STING to prevent sustained innate immune signaling. Cell 155(3), 688-698 (2013).

    5. Gao, P., Ascano, M., Zillinger, T., et al. Structure-function analysis of STING activation by c[G(2',5')pA(3',5')p] and targeting by antiviral DMXAA. Cell 154(4), 748-762 (2013).