An internal standard for the quantification of 2’3’-cGAMP
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Unlabeled Version(s)
198872'3'-cGAMP (sodium salt)
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2'3'-cGAMP-d8 (ammonium salt)

Item No. 39608

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,7R,8R,12aR,14R,15R,15aS,16R)-7-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-14-(6-amino-9H-purin-9-yl)-15,16-dihydroxyoctahydro-12H-5,8-methanofuro[3,2-l][1,3,6,9,11]pentaoxa[2,10]diphosphacyclotetradecine-2,10-bis(olate)-4,4,5,12,12,12a,15a,16-d8 2,10-dioxide, diammonium salt
Synonyms
  • Guanosine-Adenosine 2',3'-cyclic monophosphate-d8
  • 2'3'-Cyclic GMP-AMP-d8
Molecular Formula
C20H14D8N10O13P2 • 2NH4
Formula Weight
716.5
Purity
≥99% deuterated forms (d1-d8)
Formulation (Request formulation change)
A 1:1 solution in acetonitrile:water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O=P1([O-])O[C@]([C@@H](O)[C@H](N2C=NC3=C2N=CN=C3N)O4)([2H])[C@@]4([2H])C([2H])([2H])OP(O[C@@]5([H])[C@H](N6C=NC7=C6NC(N)=NC7=O)O[C@]([C@@]5([2H])O)([2H])C([2H])([2H])O1)([O-])=O.[NH4+].[NH4+]
InChi Code
InChI=1S/C20H24N10O13P2.2H3N/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33;;/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33);2*1H3/t6-,7-,10-,11-,12-,13-,18-,19-;;/m1../s1/i1D2,2D2,6D,7D,10D,12D;;
InChi Key
HYNJYAVPXNPUTJ-JDLSNETKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    250 µg

    $659

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    Product Description

    2’3’-cGAMP-d8 is intended for use as an internal standard for the quantification of 2’3’-cGAMP (Item No. 19887) by GC- or LC-MS. 2’3’-cGAMP is a second messenger produced from ATP and GTP by cGMP-AMP synthase (cGAS) in the cytoplasm of mammalian cells in response to the presence of dsDNA.1,2,3 It contains a non-canonical 2’5’-phosphodiester bond and binds tightly to the adapter protein stimulator of interferon genes (STING) with a Kd value of 3.79 nM, which is significantly lower than that observed for 2’2’-cGAMP (Item No. 22419), 3’3’-cGAMP (Item No. 17966), cyclic di-GMP (Item No. 17144), and 3’2’-cGAMP (Kds = 0.287, 1.04, 1.21, and 1.61 µM, respectively).3 It is a potent inducer of IFN-β mRNA expression with an EC50 value of 19.4 nM in L929 cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wu, J., Sun, L., Chen, X., et al. Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA. Science 339(6121), 826-830 (2013).

    2. Sun, L., Wu, J., Du, F., et al. Cyclic GMP-AMP synthase is a cytosolic DNA sensor that activates the type I interferon pathway. Science 339(6121), 786-791 (2013).

    3. Zhang, X., Shi, H., Wu, J., et al. Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING. Mol. Cell 51(2), 226-235 (2013).