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Merck

SML1231

Sigma-Aldrich

c-di-AMP sodium salt

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

Sinónimos:

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

Fórmula empírica (notación de Hill):
C20H24N10O12P2 · xNa+
Número de CAS:
Peso molecular:
658.41 (free acid basis)
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

c-di-AMP sodium salt, ≥98% (HPLC)

description

contains 1μmol of powder (approx. 0.7mg)

Quality Level

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

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

Referencia del producto
Descripción
Precios

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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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