An internal standard for the quantification of cyclic di-GMP
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Unlabeled Version(s)
17144Cyclic di-GMP (sodium salt)
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13C20,15N10-Cyclic di-GMP (sodium salt)

Item No. 36245

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,9-bis(2-(amino-15N)-6-oxo-1,6-dihydro-9H-purin-9-yl-13C5-15N4)-3,10-dihydroxyoctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9]tetraoxa[2,8]diphosphacyclododecine-5,12-bis(olate)-2R,3R,3aS,7,7aR,9R,10R,10aS,14,14aR-13C10 5,12-dioxide, disodium salt
Synonyms
  • 13C20,15N10-c-di-GMP
  • 13C20,15N10-Cyclic diguanylate
  • 13C20,15N10-3’,5’-Cyclic diguanylic Acid
Molecular Formula
[13C]20H22[15N]10O14P2 • 2Na
Formula Weight
764.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: soluble
SMILES
O=[13C]1[15NH][13C]([15NH2])=[15N][13C]2=[13C]1[15N]=[13CH][15N]2[13C@@H]([13C@@H]3O)O[13C@@]([H])([13C@]3(OP([O-])(O[13CH2][13C@]([H])([13C@]4(O5)[H])O[13C@H]([13C@@H]4O)[15N]6[13C]([15N]=[13C]([15NH]7)[15NH2])=[13C]([15N]=[13CH]6)[13C]7=O)=O)[H])[13CH2]OP5([O-])=O.[Na+].[Na+]
InChi Code
InChI=1S/C20H24N10O14P2.2Na/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34;;/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34);;/q;2*+1/p-2/t5-,6-,9-,10-,11-,12-,17-,18-;;/m1../s1/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1,10+1,11+1,12+1,13+1,14+1,15+1,16+1,17+1,18+1,19+1,20+1,21+1,22+1,23+1,24+1,25+1,26+1,27+1,28+1,29+1,30+1;;
InChi Key
SVIXOIGPVFFABR-PCSBNXRQSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    13C20,15N10-Cyclic di-GMP is intended for use as an internal standard for the quantification of cyclic di-GMP (Item No. 17144) by GC- or LC-MS. Cyclic di-GMP is a second messenger in bacteria involved in diverse prokaryotic processes, including biofilm formation, motility, virulence, and cell cycling.1,2 In eukaryotic cells, cyclic di-GMP is detected by and binds to the transmembrane protein stimulator of interferon genes (STING; Kd = 1.21 µM), leading to activation of the innate immune system.3,4 It has been used at a preset molar ratio with STING dimers in binding assays to determine the binding constants of particularly tight binding partners, such as 2’3’-cGAMP. Cyclic di-GMP induces IFN-β mRNA expression in vitro (EC50 = 537.8 nM) but less potently than 2’3’-cGAMP (Item No. 19887), 3’2’-cGAMP, 3’3’-cGAMP (Item No. 17966), and 2’2’-cGAMP (Item No. 22419).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Martínez, L.C., and Vadyvaloo, V. Mechanisms of post-transcriptional gene regulation in bacterial biofilms. Front. Cell. Neurosci. 4(38), 1-15 (2014).

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

    4. 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).