2',3'-cGAMP

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Physical properties

Molecular weight	674.42
Solvent	DMSO

Storage, safety and handling

Intended use	Research Use Only (RUO)
Storage	Freeze (< -15 °C); Minimize light exposure

Overview SDS Protocol

Molecular weight

674.42

2',3'-cGAMP or cGAMP (Cyclic guanosine monophosphate"adenosine monophosphate) is produced in mammalian cells by cGAS (cGAMP synthase) from ATP and GTP upon cytosolic DNA stimulation. cGAMP produced by cGAS contains mixed phosphodiester linkages, with one between 2'-OH of GMP and 5'-phosphate of AMP and the other between 3'-OH of AMP and 5'-phosphate of GMP. 2',3'-cGAMP is also referred to as "noncanonical" cGAMP due to the presence of the atypical 2'-5' phosphodiester linkage between the guanosine and the adenosine. Similar to the canonical 3',3'-cGAMP, 2'3'-cGAMP serves as a second messenger to activate innate immune responses by binding to STING (stimulator of IFN genes) and subsequently inducing the TBK1-IRF3-dependent production of IFN-β. Structural and functional studies revealed that noncanonical 2'3'-cGAMP is distinct from the canonical 3'3'-cGAMP produced by bacteria. 2'3'-cGAMP binds to STING with a much greater affinity than 3'3'-cGAMP. cGAMP has also been shown to be an effective adjuvant that boosts the production of antigen-specific antibodies and T cell responses in mice. cGAMP demonstrates antiviral functions in the cell where it is produced, it can cross cell membranes by passive diffusion to have some effects on neighboring cells.

Calculators

Common stock solution preparation

Table 1. Volume of DMSO needed to reconstitute specific mass of 2',3'-cGAMP to given concentration. Note that volume is only for preparing stock solution. Refer to sample experimental protocol for appropriate experimental/physiological buffers.

	0.1 mg	0.5 mg	1 mg	5 mg	10 mg
1 mM	148.276 µL	741.378 µL	1.483 mL	7.414 mL	14.828 mL
5 mM	29.655 µL	148.276 µL	296.551 µL	1.483 mL	2.966 mL
10 mM	14.828 µL	74.138 µL	148.276 µL	741.378 µL	1.483 mL

Molarity calculator

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Images

Figure 1. Chemical structure for 2',3'-cGAMP.

Citations

View all 55 citations: Citation Explorer

The cGAS-cGAMP-STING Pathway: A Molecular Link Between Immunity and Metabolism
Authors: Bai, J., Liu, F.
Journal: Diabetes (2019): 1099-1108

Efficacy and mechanism of cGAMP to suppress Alzheimer's disease by elevating TREM2
Authors: Xu, Q., Xu, W., Cheng, H., Yuan, H., Tan, X.
Journal: Brain Behav Immun (2019): se name="20310.enl" path="C:\Users\aatbi\Drop

Discovery of a Novel cGAMP Competitive Ligand of the Inactive Form of STING
Authors: Siu, T., Altman, M. D., Baltus, G. A., Childers, M., Ellis, J. M., Gunaydin, H., Hatch, H., Ho, T., Jewell, J., Lacey, B. M., Lesburg, C. A., Pan, B. S., Sauvagnat, B., Schroeder, G. K., Xu, S.
Journal: ACS Med Chem Lett (2019): 92-97

Publisher Correction: Viral and metazoan poxins are cGAMP-specific nucleases that restrict cGAS-STING signalling
Authors: Eaglesham, J. B., Pan, Y., Kupper, T. S., Kranzusch, P. J.
Journal: Nature (2019): E12

The STING ligand cGAMP potentiates the efficacy of vaccine-induced CD8+ T cells
Authors: Gutjahr, A., Papagno, L., Nicoli, F., Kanuma, T., Kuse, N., Cabral-Piccin, M. P., Rochereau, N., Gostick, E., Lioux, T., Perouzel, E., Price, D. A., Takiguchi, M., Verrier, B., Yamamoto, T., Paul, S., Appay, V.
Journal: JCI Insight (2019): se name="20310.enl" path="C:\Users\aatbi\Drop

SLC19A1 Is an Importer of the Immunotransmitter cGAMP
Authors: Ritchie, C., Cordova, A. F., Hess, G. T., Bassik, M. C., Li, L.
Journal: Mol Cell (2019): 372-381 e5

A Click-Chemistry Linked 2'3'-cGAMP Analogue
Authors: Dialer, C. R., Stazzoni, S., Drexler, D. J., Muller, F. M., Veth, S., Pichler, A., Okamura, H., Witte, G., Hopfner, K. P., Carell, T.
Journal: Chemistry (2019): 2089-2095

Distinct Dynamic and Conformational Features of Human STING in Response to 2'3'-cGAMP and c-di-GMP
Authors: Guo, J., Wang, J., Fan, J., Zhang, Y., Dong, W., Chen, C. P.
Journal: Chembiochem (2019): 1838-1847

A Poxin on Both of Your Houses: Poxviruses Degrade the Immune Signal cGAMP
Authors: Dippel, A. B., Hammond, M. C.
Journal: Biochemistry (2019): 2387-2388

Structure and mechanism of a Hypr GGDEF enzyme that activates cGAMP signaling to control extracellular metal respiration
Authors: Hallberg, Z. F., Chan, C. H., Wright, T. A., Kranzusch, P. J., Doxzen, K. W., Park, J. J., Bond, D. R., Hammond, M. C.
Journal: Elife (2019): se name="20310.enl" path="C:\Users\aatbi\Drop