0 Items - $0.00
Categories
A to Z

c[G(2',5')pA(3',5')p] / 2'3'-cGAMP

Cyclic (guanosine- (2' −> 5')- monophosphate- adenosine- (3' −> 5')- monophosphate) ( c[G(2',5')pA(3',5')p] / cGAMP(2'-5') / 2'3'-cGAMP / 2',5'-3',5'-cGAMP ), sodium salt
Metazoan cyclic dinucleotide second messenger
Cat. No.: C 161
    
CAS No.: [1441190-66-4]
Shipping: ambient
Product Name Price (net) Qty
Cat. No.: C 161-005
Unit: 0.5 µmol / ~337 µg
$150.00

For other salt forms please inquire.c[G(2',5')pA(3',5')p] was found to be the metazoan second messenger produced by the mammalian innate immune DNA sensor cGAMP synthase (cGAS). It has also been reported to exert potent activation of the immune signalling protein STING. Detailed technical information available. References: Gao et al., Cell, 153, 1094 - 1107 (2013); Ablasser et al., Nature, 498, 380 - 384 (2013); Zhang et al., Mol. Cell, 51, 226 - 235 (2013); Diner et al., Cell Rep., 3, 1355 - 1361 (2013).

Related products: Biolog also offers the potential bacterial second messenger c[G(3',5')pA(3',5')p] (c-(ApGp), Cat. No. C 117).

Cat. No. C 161
CAS number [1441190-66-4]
Purity > 98% HPLC
Salt form Sodium
Storage temperature -20°C / -4°F
Molecular formula C₂₀H₂₄N₁₀O₁₃P₂ (free acid)
Molecular weight [g/mol] 674.4 (free acid)
Absorption max [nm] 256
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 25050
  • 1. Bridgeman A., Maelfait J., Davenne T., Partridge T., Peng Y., Mayer A., Dong T., Kaever V., Borrow P.Rehwinkel J., Science, 349, 1228 - 1232 (2015), "Viruses Transfer the Antiviral Second Messenger cGAMP Between Cells"
  • 2. Li W., Cui T., Hu L., Wang Z., Li Z.He Z.-G., Nature Communications, 0, 0 - 0 (2015), "Cyclic Diguanylate Monophosphate Directly Binds to Human Siderocalin and Inhibits its Antibacterial Activity"
  • 3. Shi H., Wu J., Chen Z. J.Chen C., Proc. Natl. Acad. Sci. USA, 112, 8947 - 8952 (2015), "Molecular Basis for the Specific Recognition of the Metazoan Cyclic GMP-AMP by the Innate Immune Adaptor Protein STING"
  • 4. Gundlach J., Dickmanns A., Schröder-Tittmann K., Neumann P., Kaesler J., Kampf J., Herzberg C., Hammer E., Schwede F., Kaever V., Tittmann K., Stülke J.Ficner R., J.Biol.Chem., 290, 3069 - 3080 (2015), "Identification, Characterization, and Structure Analysis of the Cyclic di-AMP-binding PII-like Signal Transduction Protein DarA"
  • 5. Gao J., Tao J., Liang W., Zhao M., Du X., Cui S., Duan H., Kan B., Su X.Jiang Z., Cell Res., 25, 539 - 550 (2015), "Identification and Characterization of Phosphodiesterases that Specifically Degrade 3'3'-cyclic GMP-AMP"
  • 6. Lolicato M., Bucchi A., Arrigoni C., Zucca S., Nardini M., Schroeder I., Simmons K., Aquila M., DiFrancesco D., Bolognesi M., Schwede F., Kashin D., Fishwick C. W. G., Johnson A. P., Thiel G.Moroni A., Nat. Chem. Biol., 10, 457 - 462 (2014), "Cyclic Dinucleotides bind the C-linker of HCN4 to Control Channel cAMP Responsiveness"
  • 7. Li L., Yin Q., Kuss P., Maliga Z., Millan J. L., Wu H.Mitchison T. J., Nat. Chem. Biol., 10, 1043 - 1048 (2014), "Hydrolysis of 2'3'-cGAMP by ENPP1 and Design of Nonhydrolyzable Analogs"
  • 8. Zhang X., Shi H., Wu J., Zhang X. W., Sun L., Chen C.Chen Z. J., Mol. Cell, 51, 226 - 235 (2013), "Cyclic GMP-AMP Containing Mixed Phosphodiester Linkages is An Endogenous High-Affinity Ligand for STING"
  • 9. Ablasser A., Goldeck M., Cavlar T., Deimling T., Witte G., Röhl I., Hopfner K.-P., Ludwig J.Hornung V., Nature, 498, 380 - 384 (2013), "cGAS Produces a 2'-5'-Linked Cyclic Dinucleotide Second Messenger that Activates STING"
  • 10. Gao P., Ascano M., Wu Y., Barchet W., Gaffney B. L., Zillinger T., Serganov A. A., Liu Y., Jones R. A., Hartmann G., Tuschl T.Patel D. J., Cell, 153, 1094 - 1107 (2013), "Cyclic [G(2',5')pA(3',5')p] Is the Metazoan Second Messenger Produced by DNA-Activated Cyclic GMP-AMP Synthase"
  • 11. Diner E. J., Burdette D. L., Wilson S. C., Monroe K. M., Kellenberger C. A., Hyodo M., Hayakawa Y., Hammond M. C.Vance R. E., Cell Rep., 3, 1355 - 1361 (2013), "The Innate Immune DNA Sensor cGAS Produces a Noncanonical Cyclic Dinucleotide that Activates Human STING"
  • 12. Gao D., Wu J., Wu Y. T., Du F., Aroh C., Yan N., Sun L.Chen Z. J., Science, 341, 903 - 906 (2013), "Cyclic GMP-AMP Synthase is an Innate Immune Sensor of HIV and Other Retroviruses"
  • 13. Li X. D., Wu J., Gao D., Wang H., Sun L.Chen Z. J., Science, 341, 1390 - 1394 (2013), "Pivotal Roles of cGAS-cGAMP Signaling in Antiviral Defense and Immune Adjuvant Effects"
  • 14. Civril F., Deimling T., de Oliveira Mann C. C., Ablasser A., Moldt M., Witte G., Hornung V.Hopfner K.-P., Nature, 498, 332 - 337 (2013), "Structural Mechanism of Cytosolic DNA Sensing by cGAS"
  • 15. Ablasser A., Schmid-Burgk J. L., Hemmerling I., Horvath G. L., Schmidt T., Latz E.Hornung V., Nature, 503, 530 - 534 (2013), "Cell Intrinsic Immunity Spreads to Bystander Cells via the Intercellular Transfer of cGAMP"
  • 16. Danilchanka O.Mekalanos J. J., Cell, 154, 962 - 970 (2013), "Cyclic Dinucleotides and the Innate Immune Response"
  • 17. Konno H., Konno K.Barber G. N., Cell, 155, 688 - 698 (2013), "Cyclic Dinucleotides Trigger ULK1 (ATG1) Phosphorylation of STING to Prevent Sustained Innate Immune Signaling"
  • 18. Schaap P., IUBMB Life, 65, 65, 897 - 903 (2013), "Cyclic di-Nucleotide Signaling Enters the Eukaryote Domain"
  • 19. Yi G., Brendel V. P., Shu C., Li P., Palanathan S.Kao C. C., PLoS One., 8(10), 0, 0 - 0 (2013), "Single Nucleotide Polymorphisms of Human STING Can affect Innate Immune Response to Cyclic Dinucleotides"