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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)

Related Categories

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

11 - Combustible Solids

wgk_germany

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
0000316673
0000316673
SLCN0256
SLBZ0355
SLBV6358

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A Ogilvie et al.
Journal of autonomic pharmacology, 16(6), 325-328 (1996-12-01)
1. Adenine dinucleotides (Ap3A, Ap4A, Ap5A, Ap6A) are stored in secretory granules of thrombocytes, chromaffin cells and neuronal cells. After release into the extracellular space, the dinucleotides exhibit divergent biological effects on a variety of target cells and organs. The
E J Verspohl et al.
Diabetes, 47(11), 1727-1734 (1998-10-29)
A role of diadenosine polyphosphates as second messengers was suggested for insulin-secreting cells. It has not yet been investigated whether specific receptors for these compounds exist and how these extracellular compounds and their degradation products may contribute to insulin release.
M Edgecombe et al.
Cellular signalling, 10(7), 505-509 (1998-10-01)
Diadenosine polyphosphates (ApnAs) can, through interaction with appropriate purinoceptors, affect a range of cellular activities. Ap4A, the most prominent naturally occurring diadenosine polyphosphate, stimulates alterations in intracellular calcium homeostasis and subsequent activation of glycogen breakdown in isolated liver cells. Here
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)
An investigation into the role of ATP in the mammalian pre-mRNA 3? cleavage reaction
Khleborodova A, et al.
Biochimie, 125, 213-222 (2016)
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