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D4022

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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2 mg

Available to ship TODAYfromMILWAUKEE

$78.60
10 mg

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$185.00
25 mg

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$380.00
50 mg

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$651.00

About This Item

Linear Formula:
C20H29N10O22P5 · 5 Na
CAS Number:
4097-04-5
Molecular Weight:
1026.28
NACRES:
NA.51
PubChem Substance ID:
24893808
eCl@ss:
32160414
EC Number:
223-852-7
MDL number:
MFCD00077718
Beilstein/REAXYS Number:
4949216
UNSPSC Code:
12352208

$78.60

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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

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.
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.

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This Item
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P1,P5-Di(adenosine-5′) pentaphosphate pentasodium salt ≥95% (HPLC), powder

Sigma-Aldrich

D4022

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

P1,P5-Di(adenosine-5′) pentaphosphate ammonium salt ≥95% (HPLC), powder

Sigma-Aldrich

D8013

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

P1,P5-Di(adenosine-5′) pentaphosphate trilithium salt ≥95%, powder

Sigma-Aldrich

D6392

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

Adenosine 3′,5′-diphosphate disodium salt ≥96%

Sigma-Aldrich

A5763

Adenosine 3′,5′-diphosphate disodium salt

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (inorganic)

assay

≥95% (HPLC)

assay

≥95% (HPLC)

assay

≥95%

assay

≥96%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

solubility

H2O: 50 mg/mL

solubility

H2O: 50 mg/mL

solubility

H2O: 50 mg/mL

solubility

water: 25 mg/mL, clear, colorless to very faintly yellow

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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
0000540498
0000540496
0000521357
0000521357
0000540498

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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)
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)
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)
View All Related Papers

Global Trade Item Number

SKUGTIN
D4022-50MG04061832947280
D4022-2MG04061833563915
D4022-25MG04061833563908
D4022-10MG04061833563885

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