cGAMP
- 2',3'-cyclic GMP-AMP Sodium salt
- Parent CAS: 1441190-66-4
- Optical Purity: 99% e.e.
- Soluble in water
- MF: C20H22N10Na2O13P2
- MW: 718.37
Description
2′,3′-cGAMP (cyclic [G(2’,5’)pA(3’,5’)p]) is the endogenous agonist for the STING (STimulator of INterferon Genes), a receptor crucial to activate the innate immune system. It is a noncanonical cyclic dinucleotide (CDN) produced as a second messenger in mammalian cells by the cytosolic cGAS (cGAMP synthase) in response to double-stranded DNA in the cytoplasm. The binding potency of noncanonical 2′,3′-cGAMP for human STING is much better than that of the canonical 3′,3′-cyclic dinucleotides (CDNs) produced in bacterial, with a Kd of 4.6 nM compared to >1 μM for bacterial 3′,3′-CDNs.
More Information
| Parent CAS No. | 1441190-66-4 |
|---|---|
| Chemical Name | N.A. |
| extra_info | Sold in collaboration with Chemietek |
| SMILES | C12C(=O)NC(N)=NC=1N([C@H]1[C@@H]3O[P@](OC[C@@H]4[C@H]([C@@H](O)[C@H](N5C6N=CN=C(N)C=6N=C5)O4)O[P@](=O)(O[Na])OC[C@H]([C@H]3O)O1)(=O)O[Na])C=N2 |&1:9,10,12,15,16,17,19,32,38,39,r| |
| MFCD | N.A. |
| InChi | InChI=1S/C20H24N10O13P2.2Na/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);;/q;2*+1/p-2/t6-,7-,10-,11-,12-,13-,18-,19-;;/m1../s1 |
| InChiKey | CNVCOPPPOWRJAV-DQNSRKNCSA-L |
| CID | 137025392 |
| Short Description | STING agonist |
References
- X. Zhang et al. Cyclic GMP-AMP containing mixed phosphdiester linkages is an endogenous high-affinity ligand for STING. Mol Cell. 2013, 51, 226-235.
- E. Diner et al. The Innate Immune DNA Sensor cGAS Produces a Noncanonical Cyclic Dinucleotide that Activates Human STING. Cell Rep. 2013, 3, 1355-1361.
- P. Gao et al.Cyclic [G(2',5')pA(3',5')p] is the metazoan second messenger produced by DNA-activated cyclic GMP-AMP synthase. Cell. 2013, 153, 1094-10107.
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