Cyclic di-AMP

Base Information

• Chemical Name: Cyclic di-AMP
• CAS No.: 54447-84-6
• Molecular Formula: C20H24N10O12P2
• Molecular Weight: 658.41
• UNII: WH9B66EIX2
• DSSTox Substance ID: DTXSID201317771
• Nikkaji Number: J2.327.567H
• Wikipedia: Cyclic_di-AMP
• Wikidata: Q27139726
• Pharos Ligand ID: YGUFHWPRKS2G
• Metabolomics Workbench ID: 65782
• ChEMBL ID: CHEMBL1229884
• Mol file: 54447-84-6.mol

Synonyms:c-di-AMP;cyclic di-AMP;cyclic diadenosine phosphate

Chemical Property of Cyclic di-AMP

Chemical Property:

• Boiling Point: 1096.7±75.0 °C(Predicted)
• PKA: 0.96±0.70(Predicted)
• PSA: 329.30000
• Density: 2.52±0.1 g/cm3(Predicted)
• LogP: -0.47240
• Storage Temp.: -20°C
• XLogP3: -5.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 2
• Exact Mass: 658.10504023
• Heavy Atom Count: 44
• Complexity: 1080

Purity/Quality:

97% ^*data from raw suppliers

Cyclicdi-AMP ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O
• Isomeric 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
• Uses: Cyclic di-AMP (c-di-AMP) is a second messenger produced by bacteria. It impacts bacterial cell growth, cell wall homeostasis, pathogenicity, and other cellular functions.

Technology Process of Cyclic di-AMP

There total 13 articles about Cyclic di-AMP which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 21.0%

ATP (56-65-5,896506-78-8) + 2-chloro-ATP (185341-71-3) → cyclic (adenosine-(3'→5')-monophosphate-8-chloroadenosine-(3'→5')-monophosphate) + cyclic (8-chloroadenosine-(3'→5')-monophosphate-8-chloroadenosine-(3'→5')-monophosphate) + c-di-AMP (54447-84-6)

Guidance literature:

With ethanolamine; magnesium chloride; D,L-dithiothreitol; In aq. buffer; at 37 ℃; for 72h; pH=9.5; Enzymatic reaction;

Reference yield:

ATP (56-65-5,896506-78-8) + benzimidazole riboside-5'-O-triphosphate → cyclic (adenosine-(3'→5')-monophosphate-benzimidazole riboside-(3'→5')-monophosphate) + cyclic (benzimidazole riboside-(3'→5')-monophosphate-benzimidazole riboside-(3'→5')-monophosphate) + c-di-AMP (54447-84-6)

Guidance literature:

With ethanolamine; magnesium chloride; D,L-dithiothreitol; In aq. buffer; at 30 - 37 ℃; for 72h; pH=9.5; Overall yield = 75 percent; Enzymatic reaction;

Reference yield:

5,6-dichlorobenzimidazole riboside-5'-O-triphosphate + ATP (56-65-5,896506-78-8) → cyclic (5,6-dichlorobenzimidazole riboside-(3'→5')-monophosphate-5,6-dichlorobenzimidazole riboside-(3'→5')-monophosphate) + cyclic (adenosine-(3'→5')-monophosphate-5,6-dichlorobenzimidazole riboside-(3'→5')-monophosphate) + c-di-AMP (54447-84-6)

Guidance literature:

With ethanolamine; magnesium chloride; D,L-dithiothreitol; In aq. buffer; at 30 - 37 ℃; for 48h; pH=9.5; Overall yield = 75 percent; Enzymatic reaction;

upstream raw materials:

adenosine 5'-phosphorimidazolide

ATP

2-chloro-ATP