SML3293
3′,2′-Cgamp Disodium
≥98% (HPLC)
Synonym(s):
Adenylyl-(2′→5′)-3′-guanylic acid cyclic nucleotide disodium
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About This Item
Empirical Formula (Hill Notation):
C20H22N10O13P2 ·2Na
Molecular Weight:
718.38
UNSPSC Code:
51111800
NACRES:
NA.77
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to beige
storage temp.
−20°C
SMILES string
NC1=NC=NC2=C1N=CN2[C@H]3[C@H](OP4([O-])=O)[C@H](O)[C@@H](COP([O-])(O[C@H]5[C@@H](O)[C@H](N(C=N6)C7=C6C(NC(N)=N7)=O)O[C@@H]5CO4)=O)O3.[Na].[Na+]
General description
3’,2’-cGAMP is a signaling molecule produced by the host immune system in response to pathogens. 3’,2’-cGAMP is synthesized from CdnG , one of the Cyclic-oligonucleotide-based antiphage signaling systems (CBASS). It activates the stimulator of interferon genes (STING)effector protein to initiate a potent interferon response. The drosophila STING (dSTING) in complex with 3′2′-cGAMP explains selective isomer recognition.
Biochem/physiol Actions
3′,2′-cGAMP is a bacterial second messenger involved in antiphage defense system. 3′,2′-cGAMP is a signaling molecule that activates Cap5 for DNA degradation in Asticcacaulis sp. and Lactococcus lactis. 3′2′-cGAMP is produced upon in Drosophila melanogaster upon activation by viral RNA or DNA of cGAS-like receptors (cGLRs) and induces antiviral response.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Pivotal Roles of cGAS-cGAMP Signaling in Antiviral Defense and Immune Adjuvant Effects
LI ZG, et al.
Science (2013)
Shirin Fatma et al.
Nature communications, 12(1), 6381-6381 (2021-11-06)
Cyclic-oligonucleotide-based antiphage signaling systems (CBASS) are diverse and abundant in bacteria. Here, we present the biochemical and structural characterization of two CBASS systems, composed of CdnG and Cap5, from Asticcacaulis sp. and Lactococcus lactis. We show that CdnG from Asticcacaulis
Kailey M Slavik et al.
Nature, 597(7874), 109-113 (2021-07-15)
Cyclic GMP-AMP synthase (cGAS) is a cytosolic DNA sensor that produces the second messenger cG[2'-5']pA[3'-5']p (2'3'-cGAMP) and controls activation of innate immunity in mammalian cells1-5. Animal genomes typically encode multiple proteins with predicted homology to cGAS6-10, but the function of
Andreas Holleufer et al.
Nature, 597(7874), 114-118 (2021-07-15)
In mammals, cyclic GMP-AMP (cGAMP) synthase (cGAS) produces the cyclic dinucleotide 2'3'-cGAMP in response to cytosolic DNA and this triggers an antiviral immune response. cGAS belongs to a large family of cGAS/DncV-like nucleotidyltransferases that is present in both prokaryotes1 and
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