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

SIGMA/D4022 - ≥95% (HPLC), powder

Synonym: A(5′)P5(5′)A; Diadenosine pentaphosphate pentasodium salt

CAS Number: 4097-04-5
Empirical Formula (Hill Notation): C₂₀H₂₄N₁₀Na₅O₂₂P₅
Molecular Weight: 1026.28
EC Number: 223-852-7
MDL Number: MFCD00077718
Linear Formula: C₂₀H₂₉N₁₀O₂₂P₅ · 5 Na
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-D4022-2MG	2 mg	$78.60 1/EA	Add To Favorites
45-D4022-10MG	10 mg	$185.00 1/EA	Add To Favorites
45-D4022-25MG	25 mg	$380.00 1/EA	Add To Favorites
45-D4022-50MG	50 mg	$651.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: D4022-25MG

Properties
Descriptions
Safety Info.
Basic Data

assay	≥95% (HPLC)
biological source	synthetic (organic)
color	white to yellow-white
form	powder
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
mol wt	~_1.0 kDa
Quality Level	200
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
solubility	H₂O: 50 mg/mL
storage temp.	−20°C

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.
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.
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.
Packaging:	10, 25, 50 mg in poly bottle
Packaging:	2 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥95% (HPLC)
Storage Temp.	−20°C
UNSPSC	12352202

To Order From a Quote