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A9396

Sigma-Aldrich

Adenosine 2′-monophosphate

from yeast

Synonyme(s) :

Adenosine 2′-monophosphoric acid, phosphoadenosine, 2′-AMP, 2′-Adenylic acid

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About This Item

Formule empirique (notation de Hill):
C10H14N5O7P
Numéro CAS:
130-49-4
Poids moléculaire :
347.22
Code UNSPSC :
41106305
eCl@ss :
32160414
ID de substance PubChem :
24891443
Nomenclature NACRES :
NA.51

Source biologique

yeast

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

1 N NH4OH: 50 mg/mL, clear, colorless to faintly yellow

Température de stockage

−20°C

Chaîne SMILES 

NC1=NC=NC2=C1N=CN2[C@H]3[C@H](OP(O)(O)=O)[C@H](O)[C@@H](CO)O3.[H]O[H].NC4=NC=NC5=C4N=CN5[C@H]6[C@H](OP(O)(O)=O)[C@H](O)[C@@H](CO)O6

InChI

1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

Clé InChI

QDFHPFSBQFLLSW-KQYNXXCUSA-N

Description générale

Adenosine 2′-monophosphate (2’-AMP) is an adenine nucleotide having single phosphate group esterified to the sugar moiety in the 2′-position.

Application

Adenosine 2′-monophosphate (2′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP. 2′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′-AMP is used in the synthesis of a new photoaffinity lable for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase. 2′,3′-cAMP and 2′-AMP represent a new unexplored pathway for adenosine-based cell regulation.

Actions biochimiques/physiologiques

AMP serves as a key component of several compounds, including coenzyme A, which plays an essential role in energy metabolism, as well as certain key redox cofactors such as NAD+, NADP+, and FAD. Furthermore, AMP is one of the key components of RNA, which is essential for protein synthesis and other biological processes in cells.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Ying Qin et al.
Lipids in health and disease, 9, 78-78 (2010-07-27)
Non-alcoholic fatty liver disease (NAFLD), which is characterized by hepatic steatosis, can be reversed by early treatment. Several case reports have indicated that the administration of recombinant growth hormone (GH) could improve fatty liver in GH-deficient patients. Here, we investigated
Yusuke Yoshimura et al.
Steroids, 162, 108695-108695 (2020-07-11)
A variety of metabolites derived from 25-hydroxyvitamin D3 [25(OH)D3], including its 3-epimer [Epi-25(OH)D3] and 3-O-sulfate [25(OH)D3-3S], is found in human plasma/serum. We hypothesized that the 3-O-sulfate of Epi-25(OH)D3 [Epi-25(OH)D3-3S] might be present in plasma/serum. Clarifying this point could improve our
Daniel T Infield et al.
The Journal of general physiology, 150(7), 1017-1024 (2018-06-06)
Voltage-dependent activation of voltage-gated cation channels results from the outward movement of arginine-bearing helices within proteinaceous voltage sensors. The voltage-sensing residues in potassium channels have been extensively characterized, but current functional approaches do not allow a distinction between the electrostatic
Peychii Lee et al.
Bioconjugate chemistry, 16(3), 650-659 (2005-05-19)
A new photoaffinity label, adenosine 2'-monophosphate, 5'-O-[S-(4-succinimidyl-benzophenone)thiophosphate] (2'-P-AMPS-Succ-BP), has been synthesized by an initial thiophosphorylation of 2'-AMP with PSCl(3) to form 2'-AMP-5'-thiophosphate (2'-AMP-5'-SP), followed by a coupling reaction of 2'-AMP-5'-SP with benzophenone-4-maleimide to produce 2'-P-AMPS-Succ-BP. This product and its precursor
Cuiying An et al.
Applied microbiology and biotechnology, 101(20), 7535-7544 (2017-09-19)
3'-Phosphoadenosine-5'-phosphosulfate (PAPS) is the obligate cosubstrate and source of the sulfonate group in the chemoenzymatic synthesis of heparin, a commonly used anticoagulant drug. Previously, using ATP as the substrate, we had developed a one-pot synthesis to prepare PAPS with 47%
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