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Merck

01930

Adenosine 5′-monophosphate disodium salt

≥99.0% (HPLC)

Synonym(s):

5′-AMPdisodium salt,, Adenylic acid disodium salt, 5′-AMP-Na2

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About This Item

Empirical Formula (Hill Notation):
C10H12N5Na2O7P
CAS Number:
4578-31-8
Molecular Weight:
391.18
PubChem Substance ID:
329747374
eCl@ss:
32160414
UNSPSC Code:
41106305
NACRES:
NA.51
EC Number:
224-961-2
MDL number:
MFCD00065023
Beilstein/REAXYS Number:
3586732

Product Name

Adenosine 5′-monophosphate disodium salt, ≥99.0% (HPLC)

SMILES string

[Na+].[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]3O
[Na+].[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]3O

InChI key

QGXLVXZRPRRCRP-IDIVVRGQSA-L

InChI

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

biological source

microbial (Candida utilis)
synthetic

assay

≥99.0% (HPLC)

form

powder

optical activity

[α]20/D −43±2°, c = 1% in 0.5 M Na2HPO4 (dry matter)

impurities

≤26% water

Quality Level

100

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Application

Adenosine 5′-monophosphate (5′-AMP) has many uses in nature. 5′-AMP is an activator of a class of protein kinases known as AMP-activated protein kinase (AMPK). It may be used as a substrate by a variety of enzymes such as AMP-thymidine kinase (EC 2.7.1.114), AMP deaminase (EC 3.5.4.6) and 5′-nucleotidase (EC 3.1.3.5).
Adenosine 5′-monophosphate disodium salt has been used:

  • as a dissolved organic phosphorus (DOP) compound to study its rate of hydrolysis in Escherichia coli lysates
  • to induce calcium responses in Fura2-loaded osteoblast (C2-OB)
  • as a nucleotide metabolite in the medium for the isolation, culture, and identification of glioma stem cells (GSCs)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN1089
BCCK9273
BCCJ3289
BCCG4167
BCCD2719

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Xiaoyu Xu et al.
Cell death & disease, 12(3), 277-277 (2021-03-17)
Glioma stem cells (GSCs) contribute to therapy resistance and poor outcomes for glioma patients. A significant feature of GSCs is their ability to grow in an acidic microenvironment. However, the mechanism underlying the rewiring of their metabolism in low pH
Nicholas Mikolajewicz et al.
Biophysical journal, 116(10), 2009-2022 (2019-05-06)
The skeleton constantly interacts and adapts to the physical world. We have previously reported that physiologically relevant mechanical forces lead to small repairable membrane injuries in bone-forming osteoblasts, resulting in release of ATP and stimulation of purinergic (P2) calcium responses
Aric H Mine et al.
Frontiers in microbiology, 12, 641700-641700 (2021-04-27)
The availability of phosphorus limits primary production in large regions of the oceans, and marine microbes use a variety of strategies to overcome this limitation. One strategy is the production of alkaline phosphatase (APase), which allows hydrolysis of larger dissolved
Giorgia Zadra et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 16(13), 3322-3328 (2010-04-29)
Although the role of metabolic syndrome (MS) and a high fat diet in prostate cancer (PCa) risk is still a matter of intense debate, it is becoming increasingly clear that obesity can cause perturbations in metabolic pathways that contribute to
Jessica Huyet et al.
Cell chemical biology, 25(6), 666-676 (2018-03-27)
Phosphoribosyltransferases catalyze the displacement of a PRPP α-1'-pyrophosphate to a nitrogen-containing nucleobase. How they control the balance of substrates/products binding and activities is poorly understood. Here, we investigated the human adenine phosphoribosyltransferase (hAPRT) that produces AMP in the purine salvage
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