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01930

Sigma-Aldrich

Adenosine 5′-monophosphate disodium salt

≥99.0% (HPLC)

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Synonym(s):
5′-AMPdisodium salt,, Adenylic acid disodium salt, 5′-AMP-Na2
Empirical Formula (Hill Notation):
C10H12N5Na2O7P
CAS Number:
4578-31-8
Molecular Weight:
391.18
Beilstein:
3586732
EC Number:
224-961-2
MDL number:
MFCD00065023
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
329747374
NACRES:
NA.51

biological source

microbial (Candida utilis)
synthetic

Quality Level

100

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)

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
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
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
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
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)
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