A linearized form of cyclic di-GMP
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Parent Compound(s)
17144Cyclic di-GMP (sodium salt)
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5'-pGpG (sodium salt)

Item No. 33889

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5′-O-phosphonoguanylyl-(3′→5′)-guanosine, trisodium salt
Synonyms
  • c-di-GMP Control
  • Cyclic di-GMP Negative Control
Molecular Formula
C20H23N10O15P2 • 3Na
Formula Weight
774.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: soluble
SMILES
O=P(O[C@H]1[C@@H](O)[C@@](N2C(NC(N)=NC3=O)=C3N=C2)([H])O[C@@H]1COP([O-])([O-])=O)([O-])OC[C@@H]4[C@@H](O)[C@@H](O)[C@@](N5C(NC(N)=NC6=O)=C6N=C5)([H])O4.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C20H26N10O15P2.3Na/c21-19-25-13-7(15(34)27-19)23-3-29(13)17-10(32)9(31)5(43-17)1-42-47(39,40)45-12-6(2-41-46(36,37)38)44-18(11(12)33)30-4-24-8-14(30)26-20(22)28-16(8)35;;;/h3-6,9-12,17-18,31-33H,1-2H2,(H,39,40)(H2,36,37,38)(H3,21,25,27,34)(H3,22,26,28,35);;;/q;3*+1/p-3/t5-,6-,9-,10-,11-,12-,17-,18-;;;/m1.../s1
InChi Key
XZFRJGQKNIQDDO-QQWDMWIMSA-K
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'-pGpG is a linearized form of cyclic di-GMP, a bacterial second messenger that activates the host innate immune system through stimulator of interferon genes (STING).1,2,3 It is a metabolite of cyclic di-GMP (Item No. 17144) formed via hydrolysis by various phosphodiesterases (PDEs) that binds to the cyclic di-GMP-I riboswitch with reduced affinity compared to cyclic di-GMP.4,5 5'-pGpG is intended for use as a negative control for cyclic di-GMP 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. Römling, U., Galperin, M.Y., and Gomelsky, M. Cyclic di-GMP: The first 25 years of a universal bacterial second messenger. Microbiol. Mol. Biol. Rev. 77(1), 1-52 (2013).

    3. Smith, K.D., Lipchock, S.V., and Strobel, S.A. Structural and biochemical characterization of linear dinucleotide analogues bound to the c-di-GMP-I aptamer. Biochemistry 51(1), 425-432 (2012).