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D1262

Sigma-Aldrich

P1,P4-Di(adenosine-5′) tetraphosphate ammonium salt

≥95% (HPLC), powder

Synonym(s):

A(5′)p4(5′)A, Diadenosine tetraphosphate ammonium salt

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About This Item

Empirical Formula (Hill Notation):
C20H28N10O19P4 · xNH3
CAS Number:
102783-36-8
Molecular Weight:
836.39 (free acid basis)
MDL number:
MFCD00058622
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24277711
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

N.Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(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/C20H28N10O19P4.H3N/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)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)(H2,21,23,25)(H2,22,24,26);1H3/t7-,8-,11-,12-,13-,14-,19-,20-;/m1./s1

InChI key

JTLRVYSRZSPJKJ-AHKIGRPSSA-N

Gene Information

human ... PLD1(5337) , PLD2(5338) , PLD3(23646) , PLD4(122618) , PLD5(200150)

Application

P1,P4-Di(adenosine-5′) tetraphosphate ammonium salt has been used as a substrate for nudix hydrolyse. It has also been used as a ATP analog and nudix substrate for cleavage factor II Im25 subunit.

Biochem/physiol Actions

Diadenosine polyphosphate (Ap4A) functions as a second messenger in pancreatic cells. Diadenosine polyphosphate is majorly stored in neuronal cells, thrombocytes and chromaffin. It stimulates phospholipase D, fluctuates intracellular calcium levels, induces nitric oxide release, activates 5′-nucleotidase, and inhibits adenosine kinase activity in vitro. The membrane-bound ectoenzymes in endothelial cells in blood plasma and smooth muscle cell metabolize Ap4A.

Storage Class Code

11 - Combustible Solids

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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An investigation into the role of ATP in the mammalian pre-mRNA 3? cleavage reaction
Khleborodova A, et al.
Biochimie, 125, 213-222 (2016)
R H Hilderman et al.
FEBS letters, 427(3), 320-324 (1998-06-24)
Since the infusion of P1,P4-diadenosine 5' tetraphosphate (Ap4A) into animal models induces vasodilation [1,2], the present study was performed to determine whether Ap4A induces the release of nitric oxide (NO) from endothelial cells. Ap4A induced NO release was 4.2-fold greater
M Edgecombe et al.
The Biochemical journal, 323 ( Pt 2), 451-456 (1997-04-15)
Diadenosine polyphosphates released into the extracellular environment influence a variety of metabolic and other cellular activities in a wide range of target tissues. Here we have studied the impact of these novel nucleotides on gluconeogenesis in isolated rat proximal tubules.
Diadenosine polyphosphate-mediated activation of phospholipase D in isolated rat liver cells
Edgecombe M, et al.
Cellular Signalling, 10(7), 505-509 (1998)
The Ralstonia solanacearum effector RipN suppresses plant PAMP-triggered immunity, localizes to the endoplasmic reticulum and nucleus, and alters the NADH/NAD+ ratio in Arabidopsis
Sun Y, et al.
Molecular Plant Pathology, 20(4), 533-546 (2019)
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