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Merck

SML1229

Sigma-Aldrich

2′,3′-cGAMP sodium salt

≥98% (HPLC)

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Sinónimos:
2′,5′-3′,5′-cGAMP, Cyclic [G(2′,5′)pA(3′,5′)p], cGAMP(2′-5′), c[G(2′,5′)pA(3′,5′)p] sodium salt
Fórmula empírica (notación de Hill):
C20H24N10O13P2 · xNa+
Número de CAS:
Peso molecular:
674.41 (free acid basis)
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

description

contains 0.5μmol of powder (approx. 0.335mg)

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

storage temp.

−20°C

SMILES string

O=C1N=C(N)NC2=C1N=CN2[C@H](O3)[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](O)[C@H]3COP5(O)=O

InChI

1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1

InChI key

XRILCFTWUCUKJR-INFSMZHSSA-N

Application

2′,3′-cGAMP sodium salt has been used to identify small compounds capable of binding human stimulator of interferon genes (STING). It is also used to study type I interferon response to cytosolic DNA.

Biochem/physiol Actions

2′,3′-cGAMP (cyclic [G(2′,5′)pA(3′,5′)p]) is the natural agonist for the STING (STimulator of INterferon Genes) pathway, discovered to be a pathway for antiviral innate immunity. 2′3′-cGAMP is a second messenger produced in mammalian cells by the cytosolic DNA sensor cGAS (cGAMP synthase) to activate innate immune responses by binding to STING and initiating an interferon response. The affinity of 2′3′-cGAMP for human STING is much higher than that of the bacterial 3′3′-cyclic dinucleotides (CDNs), with a Kd of 4.59 nM compared to >1 μM for bacterial 3′3′-CDNs.

Preparation Note

2′,3′-cGAMP is soluble in water and aqueous buffers (>> 5 mM, limits have not been determined).

related product

Referencia del producto
Descripción
Precios

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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