SML1231

c-di-AMP sodium salt

≥98% (HPLC)

• Synonym(s): 3′,5′-Cyclic diadenylic acid sodium salt, Adenylyl-(3′5′)-3′-adenylic acid, cyclic nucleotide sodium salt, Cyclic di-3′,5′-adenylate sodium salt, Cyclic diadenylate monophosphate sodium salt, Cyclic diadenylate sodium salt, Cyclic-di-AMP sodium salt
• Empirical Formula (Hill Notation): C₂₀H₂₄N₁₀O₁₂P₂ · xNa⁺
• CAS Number: 54447-84-6
• Molecular Weight: 658.41 (free acid basis)
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825734
• NACRES: NA.77

Properties

• description: contains 1μmol of powder (approx. 0.7mg)
• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• storage temp.: −20°C
• SMILES string: NC1=NC=NC2=C1N=CN2[C@H](O3)[C@H](O)[C@H](OP(OC[C@@H]4[C@@H](O5)[C@@H](O)[C@H](N6C=NC7=C6N=CN=C7N)O4)(O)=O)[C@H]3COP5(O)=O.C
• 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
• InChI key: PDXMFTWFFKBFIN-XPWFQUROSA-N

Description

Biochem/physiol Actions

It has a role in various signaling pathways. In Gram-positive bacteria, it influences cell growth and survival and modulates virulence. c-di-AMP is formed by diadenylate cyclases (DACs), which are cyclase domain-containing proteins.

c-di-AMP is a bacterial secondary messenger. c-di-AMP acts as a potent mucosal adjuvant stimulating both humoral and cellular responses.

Preparation Note

c-di-AMP is soluble in water (≥ 16 mM, limits have not been determined).

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable