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A3013

Sigma-Aldrich

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:
Molecular Weight:
347.22
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Maria V Papadopoulou et al.
Oncology research, 14(1), 21-29 (2003-10-14)
The enzymatic cell-free metabolism of the novel hypoxia-selective cytotoxin 4-[3-(2-nitro-1-imidazolyl)-propylamino]-7-chloroquinoline hydrochloride (NLCQ-1) was investigated under hypoxic or aerobic conditions in the presence of purified reductive enzymes or isolated rat liver microsomes by monitoring the parent compound with HPLC-UV analysis. Enzymatic
G S Padiyar et al.
Journal of biomolecular structure & dynamics, 15(4), 803-821 (1998-03-26)
Crystal structures of lithium, sodium, potassium, calcium and magnesium salts of adenosine 2'-monophosphate (2'-AMP) have been obtained at atomic resolution by X-ray crystallographic methods. 2'-AMP.Li belongs to the monoclinic space group P2(1) with a = 7.472(3)A, b = 26.853(6) A
Periprocedural type IVa myocardial infarction and the importance of platelet inhibition.
Anoop S V Shah et al.
Heart (British Cardiac Society), 99(17), 1225-1226 (2013-04-18)
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

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