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D6392

Sigma-Aldrich

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

≥95%, powder

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Synonym(s):
A(5′)P5(5′)A trilithium salt, Diadenosine pentaphosphate trilithium salt
Empirical Formula (Hill Notation):
C20H26Li3N10O22P5
CAS Number:
75522-97-3
Molecular Weight:
934.17
EC Number:
278-237-6
MDL number:
MFCD00044936
eCl@ss:
32160414
PubChem Substance ID:
24894024
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥95%

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].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/C20H29N10O22P5.3Li/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;3*+1/p-3/t7-,8-,11-,12-,13-,14-,19-,20-;;;/m1.../s1

InChI key

BFBDFBHROZLGEG-JJCYRVQFSA-K

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Application

P1,P5-Di(adenosine-5′) pentaphosphate trilithium salt has been used as a adenylate kinase inhibitor and as a component of pre-AMPPNP rigor solution for treating muscle fibres.

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 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

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Effect of adenosine triphosphate analogues on skeletal muscle fibers in rigor
Schoenberg M
Biophysical Journal, 56(1), 33-41 (1989)
Behavior of N-phenylmaleimide-and p-phenylenedimaleimide-reacted muscle crossbridge heads
Li WX and Schoenberg M
Biochimica et Biophysica Acta - Bioenergetics, 1367(1-3), 127-133 (1998)
Mitochondrial diagnostics: a multiplexed assay platform for comprehensive assessment of mitochondrial energy fluxes
Fisher-Wellman KH, et al.
Testing, 24(13), 3593-3606 (2018)

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