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Key Documents

SML1231

Sigma-Aldrich

c-di-AMP sodium salt

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

Synonyme(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

Formule empirique (notation de Hill):
C20H24N10O12P2 · xNa+
Numéro CAS:
Poids moléculaire :
658.41 (free acid basis)
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

c-di-AMP sodium salt, ≥98% (HPLC)

Description

contains 1μmol of powder (approx. 0.7mg)

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

PDXMFTWFFKBFIN-XPWFQUROSA-N

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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