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SML1231

c-di-AMP sodium salt

≥98% (HPLC), powder, bacterial second messenger

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

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About This Item

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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Product Name

c-di-AMP sodium salt, ≥98% (HPLC)

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

Biochem/physiol Actions

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

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000497052
0000497052
0000483938
0000483938
0000206732

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Qichao Sun et al.
Enzyme and microbial technology, 143, 109700-109700 (2020-12-31)
Cyclic di-AMP is a bacterial nucleotide second messenger and evaluated as a potential vaccine adjuvant candidate. Here, we report a practical and economical enzymatic method for gram-scale preparation of c-di-AMP using an immobilized Vibrio cholerae dinucleotide cyclase DncV. The method
c-di-AMP: An Essential Molecule in the Signaling Pathways that Regulate the Viability and Virulence of Gram-Positive Bacteria
Fahmi T, et al.
Genes, 8(8), 197-197 (2017)
Andrea Annibal et al.
Analytical and bioanalytical chemistry, 413(26), 6457-6468 (2021-09-04)
Cyclic dinucleotides (CDNs) are key secondary messenger molecules produced by cyclic dinucleotide synthases that trigger various cellular signaling cascades from bacteria to vertebrates. In mammals, cyclic GMP-AMP synthase (cGAS) has been shown to bind to intracellular DNA and catalyze the
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