2'3'-cGAMP

• CAT Number: R066668
• CAS Number: 1441190-66-4
• Molecular Formula: C20H24N10O13P2
• Molecular Weight: 674.4
• Purity: ≥95%
• Synonyms: 2’3′-cGAMP; Guanosine-Adenosine 2′,3′-cyclic monophosphate;2′-3′-Cyclic GMP-AMP
• Storage: -20°C
• InChI: InChI=1S/C20H24N10O13P2/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)/t6
• InChIKey: XRILCFTWUCUKJR-INFSMZHSSA-N
• SMILES: O=P1(O)O[C@]([C@@H](O)[C@H](N2C=NC3=C2N=CN=C3N)O4)([H])[C@@]4([H])COP(O[C@@]5([H])[C@H](N6C=NC7=C6NC(N)=NC7=O)O[C@]([C@H]5O)([H])CO1)(O)=O

2’3’-cGAMP (cyclic [G(2’,5’)pA(3’,5’)p]) is a cyclic dinucleotide produced in mammalian cells by cGAS (cGAMP synthase) in response of double-stranded DNA in the cytoplasm. Cyclic dinucleotides (CDNs) are a relatively new class of adjuvants that have been shown to increase vaccine potency. CDNs activate innate immunity by directly binding the endoplasmic reticulum-resident receptor STING (stimulator of interferon genes), activating a signaling pathway that induces the expression of interferon-β (IFN-β) and also nuclear factor-κB (NF-κB) dependent inflammatory cytokines.
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. Structural and functional studies revealed that noncanonical 2’3’-cGAMP is distinct from the canonical 3’3’-cGAMP produced by bacteria. Certain variants of STING are able to distinguish between noncanonical and canonical cGAMP.
Similar to the canonical 3’3’-cGAMP, 2’3’-cGAMP serves as a second messenger to activate innate immune responses by binding to STING and subsequently inducing the TBK1-IRF3 (TANK-binding kinase 1-IFN regulatory transcription factor3)-dependent production of IFN-β. Recently, it has been reported that 2’3’-cGAMP is an effective adjuvant that boosts the production of antigen-specific antibodies and T cell responses in mice.

Reference

1.Wu, J.,Sun, L.,Chen, X., et al. Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA. Science 339(6121), 826-830 (2013).