Merck
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SML1231

Sigma-Aldrich

c-di-AMP sodium salt

≥98% (HPLC)

All Photos(1)
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)
PubChem Substance ID:
329825734
NACRES:
NA.77

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

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This Item
SML1232SML1228SML1229
c-di-AMP sodium salt ≥98% (HPLC)

Sigma-Aldrich

SML1231

c-di-AMP sodium salt

cGAMP sodium salt ≥98% (HPLC)

Sigma-Aldrich

SML1232

cGAMP sodium salt

Cyclic-di-GMP sodium salt ≥98% (HPLC)

Sigma-Aldrich

SML1228

Cyclic-di-GMP sodium salt

2′,3′-cGAMP sodium salt ≥98% (HPLC)

Sigma-Aldrich

SML1229

2′,3′-cGAMP sodium salt

form

powder

form

powder

form

powder

form

powder

color

white to beige

color

white to beige

color

white to beige

color

white to beige

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

description

contains 1μmol of powder (approx. 0.7mg)

description

contains 0.5μmol of powder (approx. 0.335mg)

description

contains 1μmol of powder (approx. 0.7mg)

description

contains 0.5μmol of powder (approx. 0.335mg)

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).

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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
W Michael Babinchak et al.
Nature communications, 11(1), 5574-5574 (2020-11-06)
Liquid-liquid phase separation (LLPS) of proteins that leads to formation of membrane-less organelles is critical to many biochemical processes in the cell. However, dysregulated LLPS can also facilitate aberrant phase transitions and lead to protein aggregation and disease. Accordingly, there

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