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A3013

Adenosine 2′(3′)-monophosphate mixed isomers

Synonym(s):

Yeast adenylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H14N5O7P
CAS Number:
130-49-4
Molecular Weight:
347.22
NACRES:
NA.51
PubChem Substance ID:
24890716
UNSPSC Code:
41106305
EC Number:
204-990-7
MDL number:
MFCD00151215
eCl@ss:
32160414
Assay:
≥45% (Adenosine-3′-monophosphate, HPLC), ≥97% (Total Adenosine-3′-monophosphate; Adenosine-2′-monophosphate, HPLC), 10-55% ( Adenosine-2′-monophosphate, HPLC)
Biological source:
synthetic
Form:
powder
Solubility:
1 M NH4OH: 50 mg/mL, clear, colorless
Storage temp.:
−20°C
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biological source

synthetic

Quality Level

200

assay

≥45% (Adenosine-3′-monophosphate, HPLC), ≥97% (Total Adenosine-3′-monophosphate; Adenosine-2′-monophosphate, HPLC), 10-55% ( Adenosine-2′-monophosphate, HPLC)

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O.Nc4ncnc5n(cnc45)[C@@H]6O[C@H](CO)[C@@H](O)[C@H]6OP(O)(O)=O

InChI

1S/2C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20;11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2*2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t2*4-,6-,7-,10-/m11/s1

InChI key

UQRXDDDXDPEXNS-VQFZJOCSSA-N

General description

Adenosine 3′-monophosphate (3′-AMP) and Adenosine 2′-monophosphate (2′-AMP) are metabolites produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 2′-AMP and 3′-AMP inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.

Application

Adenosine2′(3′)-monophosphate mixed isomers have been used as a standard to separate andquantify purines (adenine and guanine) and adenine ribonucleosidemonophosphates (2’-AMP and 3’-AMP) through isocratic high-performance liquidchromatography (HPLC). It has also been used to screen the multiplesugar-binding ATPase A (MsbA) transporter protein.

Other Notes

Do not confuse with adenosine 2′:3′-cyclic monophosphate

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000519848
0000519848
0000447665
0000447663
0000447663

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Georgina Berridge et al.
The Biochemical journal, 365(Pt 1), 295-301 (2002-04-09)
Nicotinic acid-adenine dinucleotide phosphate (NAADP) is a newly described Ca2+-mobilizing nucleotide that appears to target intracellular Ca2+-release channels distinct from those sensitive to inositol trisphosphate or ryanodine/cyclic ADP-ribose. Little, however, is known concerning the regulation of cellular NAADP levels. In
Andrea A Putnam et al.
Journal of molecular biology, 425(20), 3839-3845 (2013-05-25)
In eukaryotes, cellular levels of adenosine monophosphate (AMP) signal the metabolic state of the cell. AMP concentrations increase significantly upon metabolic stress, such as glucose deprivation in yeast. Here, we show that several DEAD-box RNA helicases are sensitive to AMP
Shuji Noguchi
Protein and peptide letters, 17(12), 1559-1561 (2010-09-23)
Asparagine can be non-enzymatically deamidated and isomerized via succinimide to isoaspartate. This post-translational modification can potentially alter the physical properties or the function of the parent protein. Asn32 of ribonuclease U2A from Ustilago sphaerogena is known to rapidly deamidate and
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Global Trade Item Number

SKUGTIN
A3013-1G04061826688311
A3013-5G04061833360194