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A9376

Sigma-Aldrich

Adenosine 2′:3′-cyclic monophosphate sodium salt

≥93%

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Synonym(s):
2′,3′-cAMP sodium salt
Linear Formula:
C10H11N5O6PNa
CAS Number:
Molecular Weight:
351.19
EC Number:
MDL number:
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Assay

≥93%

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@H]4OP([O-])(=O)O[C@@H]34

InChI

1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1

InChI key

VSDSIACSNXHGOV-MCDZGGTQSA-M

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This Item
A5638A6885D0627
assay

≥93%

assay

≥95%

assay

≥98.0% (HPLC)

assay

≥96% (HPLC)

form

powder

form

powder

form

powder

form

powder

solubility

water: 50 mg/mL, clear, colorless

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

solubility

H2O: 10 mg/mL

solubility

H2O: 100 mg/mL

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

Application

Adenosine 2′:3′-cyclic monophosphate sodium salt has been used in lysis buffer for affinity purification and also in microscale thermophoresis measurements. It has also been used in electrophysiological studies of Tenebrio tubules.

Biochem/physiol Actions

Adenosine 2′,3′-cyclic monophosphate (2′,3′-cAMP) is believed to serve as an extracellular source of adenosine. The release of extracellular 2′,3′-cAMP occurs in response to injury. 2′,3′-cAMP may be used to study the distribution and specificity of its degrading enzymes in the context of unique biological activities. 2′,3′-cAMP may also be used to study apoptosis induced at the level of mitochondrial permeability transition pores. 2′,3′-cAMP is converted into 2′-AMP and 3′-AMP which inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.

Caution

Caution: Do not confuse with the common adenosine 2′(3′)-monophosphate (mixed isomers).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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C Shen et al.
Journal of molecular evolution, 31, 445-452 (1990-01-01)
The prebiotic synthesis of His and its dimer has led us to study the possible catalytic properties of His-His. The enhancing effect of His-His has been tested in the dephosphorylation of dAMP, the hydrolysis of oligo(A)12, and the oligomerization of
Edwin K Jackson et al.
The Journal of biological chemistry, 284(48), 33097-33106 (2009-10-06)
We discovered that renal injury releases 2',3'-cAMP (positional isomer of 3',5'-cAMP) into the interstitium. This finding motivated a novel hypothesis: renal injury leads to activation of an extracellular 2',3'-cAMP-adenosine pathway (i.e. metabolism of extracellular 2',3'-cAMP to 3'-AMP and 2'-AMP, which
T Uchida et al.
Biochimica et biophysica acta, 657(2), 356-363 (1981-02-13)
The sulphatase A (aryl-sulphate sulphohydrolase, EC 3.1.6.1) of ox liver hydrolyses adenosine 3',5'-monophosphate (cyclic AMP) to adenosine 5'-phosphate at an optimum pH of approx. 4.3, close that for the hydrolysis of cerebroside sulphate, a physiological substrate for sulphatase A. The
Edwin K Jackson
American journal of physiology. Renal physiology, 301(6), F1160-F1167 (2011-09-23)
Our recent studies employing HPLC-tandem mass spectrometry to analyze venous perfusate from isolated, perfused kidneys demonstrate that intact kidneys produce and release into the extracellular compartment 2',3'-cAMP, a positional isomer of the second messenger 3',5'-cAMP. To our knowledge, this represents
J Azuma et al.
Journal of molecular and cellular cardiology, 15(1), 43-52 (1983-01-01)
Trapidil, a coronary vasodilator and positive inotropic agent, was tested for its ability to affect the normal "fast" action potentials and the "slow" action potentials and contractions of isolated perfused chick hearts, and to affect the tissue cyclic AMP level.

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