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Merck

A3013

Sigma-Aldrich

Adenosine 2′(3′)-monophosphate mixed isomers

Sinónimos:

Yeast adenylic acid

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About This Item

Fórmula empírica (notación de Hill):
C10H14N5O7P
Número de CAS:
Peso molecular:
347.22
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

Quality Level

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

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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.

Linkage

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
K R Wolthers et al.
Biochemistry, 40(15), 4722-4737 (2001-04-11)
Binding of Ca(2+)-activated calmodulin (Ca(2+)-CaM) to neuronal nitric-oxide synthase (nNOS) increases the rate of 2,6-dichloroindolphenol (DCIP) reduction 2-3-fold and that of cytochrome c(3+) 10-20-fold. Parallel initial velocity patterns indicated that both substrates were reduced via two-half reactions in a ping-pong
Sergio Leonardi et al.
Heart (British Cardiac Society), 99(17), 1282-1287 (2013-02-26)
To reassess the efficacy of cangrelor efficacy using the universal definition of myocardial infarction (MI). We adopted a novel approach to systematically implement the universal definition of MI. Two physicians blinded to treatment allocation reviewed plots of CK-MB and troponin
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
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

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