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A9396

Sigma-Aldrich

Adenosine 2′-monophosphate

from yeast

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H14N5O7P
CAS Number:
130-49-4
Molecular Weight:
347.22
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24891443
NACRES:
NA.51

biological source

yeast

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

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

storage temp.

−20°C

SMILES string

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

InChI key

QDFHPFSBQFLLSW-KQYNXXCUSA-N

General description

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.

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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%
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
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
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
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
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