2'3'-cGAMP-d8 (ammonium salt)

2'3'-cGAMP-d8 is intended for use as an internal standard for the quantification of 2'3'-cGAMP (Cay-19887) by GC- or LC-MS. 2'3'-cGAMP is a second messenger produced from ATP and GTP by cGMP-AMP synthase (cGAS) in the cytoplasm of mammalian cells in response to the presence of dsDNA. It contains a non-canonical 2'5'-phosphodiester bond and binds tightly to the adapter protein stimulator of interferon genes (STING) with a Kd value of 3.79 nM, which is significantly lower than that observed for 2'2'-cGAMP (Cay-22419), 3'3'-cGAMP (Cay-17966), cyclic di-GMP (Cay-17144), and 3'2'-cGAMP (Kds = 0.287, 1.04, 1.21, and 1.61 µM, respectively). It is a potent inducer of IFN-beta mRNA expression with an EC50 value of 19.4 nM in L929 cells.Formal Name: (5R,7R,8R,12aR,14R,15R,15aS,16R)-7-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-14-(6-amino-9H-purin-9-yl)-15,16-dihydroxyoctahydro-12H-5,8-methanofuro[3,2-l][1,3,6,9,11]pentaoxa[2,10]diphosphacyclotetradecine-2,10-bis(olate)-4,4,5,12,12,12a,15a,16-d8 2,10-dioxide, diammonium salt. Synonyms: Guanosine-Adenosine 2',3'-cyclic monophosphate-d8, 2'3'-Cyclic GMP-AMP-d8. Molecular Formula: C20H14D8N10O13P2 . 2NH4. Formula Weight: 716.5. Purity: >99% deuterated forms (d1-d8). Formulation: (Request formulation change), A 1:1 solution in acetonitrile:water. Solubility: Water: Soluble. SMILES: O=P1([O-])O[C@]([C@@H](O)[C@H](N2C=NC3=C2N=CN=C3N)O4)([2H])[C@@]4([2H])C([2H])([2H])OP(O[C@@]5([H])[C@H](N6C=NC7=C6NC(N)=NC7=O)O[C@]([C@@]5([2H])O)([2H])C([2H])([2H])O1)([O-])=O.[NH4+].[NH4+]. InChi Code: InChI=1S/C20H24N10O13P2.2H3N/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),2*1H3/t6-,7-,10-,11-,12-,13-,18-,19-,,/m1../s1/i1D2,2D2,6D,7D,10D,12D,,. InChi Key: HYNJYAVPXNPUTJ-JDLSNETKSA-N.