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A2252

Sigma-Aldrich

Adenosine 5′-monophosphate monohydrate

from yeast, ≥97%

Synonym(s):

5′-AMP, A-5′-P, AMP

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About This Item

Empirical Formula (Hill Notation):
C10H14N5O7P · H2O
CAS Number:
18422-05-4
Molecular Weight:
365.24
Beilstein/REAXYS Number:
54612
MDL number:
MFCD00149360
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24890637
NACRES:
NA.51

biological source

yeast

Quality Level

200

assay

≥97%

form

powder

solubility

1 M NH4OH: soluble 50 mg/mL, clear, colorless
H2O: soluble (with addition of mild alkali)

storage temp.

−20°C

SMILES string

O[C@H]1[C@@H](O)[C@H](N(C=N2)C3=C2C(N)=NC=N3)O[C@@H]1COP(O)(O)=O.O

InChI

1S/C10H14N5O7P.H2O/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);1H2/t4-,6-,7-,10-;/m1./s1

InChI key

ZOEFQKVADUBYKV-MCDZGGTQSA-N

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Application

Adenosine 5′-monophosphate (5′AMP) is suitable for use as
  • a reagent in the synthesis of adenosine-5′-phosphoimidazolide
  • an activator of phosphorylase b in the polymerization reaction for the synthesis of branched polysaccharides
  • an inhibitor of endogenous NMN adenylyltransferase (NMNAT) activity that converts NMN to NAD+

Biochem/physiol Actions

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). AMP inhibits dephosphorylation of AMPK and promotes phosphorylation of AMPK by upstream kinases.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Physical properties and structure of enzymatically synthesized amylopectin analogs
Ciric, Jelena, et al.
Starch/Staerke, 65, 1061-1068 (2013)
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)
Marianne Suter et al.
The Journal of biological chemistry, 281(43), 32207-32216 (2006-09-01)
AMP-activated protein kinase (AMPK) is a heterotrimeric protein kinase that is crucial for cellular energy homeostasis of eukaryotic cells and organisms. Here we report on the activation of AMPK alpha1beta1gamma1 and alpha2beta2gamma1 by their upstream kinases (Ca(2+)/calmodulin-dependent protein kinase kinase-beta
Markus Hafner et al.
Methods (San Diego, Calif.), 44(1), 3-12 (2007-12-26)
Distinct classes of small RNAs, 20-32 nucleotides long, play important regulatory roles for diverse cellular processes. It is therefore important to identify and quantify small RNAs as a function of development, tissue and cell type, in normal and disease states.
Irina S Balan et al.
Brain research, 1316, 112-119 (2009-12-29)
A histo-enzymatic technique for visualizing and quantifying endogenous NAD(H) in brain tissue was developed, based on coupled enzymatic cycling reactions that reduce nitrotetrazolium blue chloride to produce formazan. Conditions were used where the endogenous level of nicotinamide adenine dinucleotides (NAD(H))
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