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Key Documents

01930

Sigma-Aldrich

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:
Molecular Weight:
391.18
Beilstein:
3586732
EC Number:
MDL number:
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.51

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

SMILES string

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

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

InChI key

QGXLVXZRPRRCRP-IDIVVRGQSA-L

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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 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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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
5′-AMP-activated protein kinase is inactivated by adrenergic signalling in adult cardiac myocytes.
Tsuchiya Y, Denison FC, et al.
Bioscience Reports, 32(2), 197-213 (2011)
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
Makhosazane Zungu et al.
The American journal of pathology, 178(1), 4-11 (2011-01-13)
The 5'-AMP-activated protein kinase (AMPK) functions as a metabolic fuel gauge that is activated in response to environmental stressors to restore cellular energy balance. In the heart, AMPK coordinates the activation of glucose and fatty acid metabolic pathways to ensure

Protocols

Separation of AMP (adenosine monophosphate); ATP (adenosine triphosphate)

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