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D4022

Sigma-Aldrich

P1,P5-Di(adenosine-5′) pentaphosphate pentasodium salt

≥95% (HPLC), powder

Synonym(s):

A(5′)P5(5′)A, Diadenosine pentaphosphate pentasodium salt

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About This Item

Linear Formula:
C20H29N10O22P5 · 5 Na
CAS Number:
4097-04-5
Molecular Weight:
1026.28
Beilstein/REAXYS Number:
4949216
EC Number:
223-852-7
MDL number:
MFCD00077718
UNSPSC Code:
12352202
eCl@ss:
32160414
PubChem Substance ID:
24893808
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

assay

≥95% (HPLC)

form

powder

mol wt

~_1.0 kDa

color

white to yellow-white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

[Na+].[Na+].[Na+].[Na+].[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6c(N)ncnc56)[C@@H](O)[C@H]3O

InChI

1S/C20H29N10O22P5.5Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30;;;;;/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26);;;;;/q;5*+1/p-5/t7-,8-,11-,12-,13-,14-,19-,20-;;;;;/m1...../s1

InChI key

NNMFUJJMJIYTSP-CSMIRWGRSA-I

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General description

P1,P5-Di(adenosine-5′) pentaphosphate (Ap5A) is a diadenosine polyphosphate, which has a tail-to-tail dimer structure. Ap5A is synthesized in a twostep process involving the formation of adenosine 5′-tetraphosphate (P4A) from the ATP and trimeta-phosphate (P3). In the second step, P4A is converted to Ap5A. The synthesis of Ap5A requires a pH optimum in the range of 7.5 to 8.5 and is modulated by metal ions.

Application

P1,P5-Di(adenosine-5′) pentaphosphate pentasodium salt has been used as:
  • an adenylate kinase (AK) inhibitor in: sarcoma osteogenic (Saos-2) cells
  • mitochondrial lysates during ATP synthesis
  • tetramethylrhodamine methyl ester (TMRM) based membrane potential assay
  • chromoplasts

Biochem/physiol Actions

A diadenosine polyphosphate stored in secretory granules of thrombocytes, chromaffin and neuronal cells. After release into the extracellular space, it affects a variety of biological activities in a wide range of target tissues. In the nervous system it acts through various purinergic receptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap5A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial and smooth muscle cells. In cardiac muscle, pM to nM concentrations significantly increase the open-probability of ryanodine-receptor (RyR2) gates, with prolonged action due to slow dissociation from the receptor.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Facile and selective synthesis of diadenosine polyphosphates through catalysis by leucyl t-RNA synthetase coupled with ATP regeneration
Nakajima H, et al.
Agricultural and Biological Chemistry, 53(3), 615-623 (1989)
Isolation of Tomato Fruit Chromoplasts and Determination of ATP Levels
Yaakov B
The Plant Journal (2013)
Soluble adenylyl cyclase-mediated cAMP signaling and the putative role of PKA and EPAC in cerebral mitochondrial function
Jakobsen E, et al.
Journal of Neuroscience Research (2019)
Polyphosphate as a donor of high-energy phosphate for the synthesis of ADP and ATP
Muller WEG, et al.
Journal of Cell Science, 130(16), 2747-2756 (2017)
Gourav Bhardwaj et al.
The Journal of clinical investigation, 131(18) (2021-08-04)
Decreased skeletal muscle strength and mitochondrial dysfunction are characteristic of diabetes. The actions of insulin and IGF-1 through the insulin receptor (IR) and IGF-1 receptor (IGF1R) maintain muscle mass via suppression of forkhead box O (FoxO) transcription factors, but whether
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