c-di-AMP

• CAT Number: I004002
• CAS Number: 54447-84-6
• Molecular Formula: C20H24N10O12P2
• Molecular Weight: 658.4
• Purity: ≥95%
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C
• IUPAC Name: (1S,6R,8R,9R,10S,15R,17R,18R)-8,17-bis(6-aminopurin-9-yl)-3,12-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.3.0.06,10]octadecane-9,18-diol
• InChI: InChI=1S/C20H24N10O12P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
• InChIKey: PDXMFTWFFKBFIN-XPWFQUROSA-N
• SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O

C-di-AMP (Cat.No:I004002) is a bacterial second messenger that binds to STING, activating the TBK3-IRF3 pathway and triggering type I IFN and TNF production. It regulates cell growth, survival, and virulence in Gram-positive bacteria and the host immune response. C-di-AMP is an effective mucosal adjuvant to stimulate immune responses.

Reference

[1]. Ren A, et al. c-di-AMP binds the ydaO riboswitch in two pseudo-symmetry-related pockets. Nat Chem Biol. 2014 Sep;10(9):780-6.