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Key Documents

D6392

Sigma-Aldrich

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

≥95%, powder

Synonym(s):

A(5′)P5(5′)A trilithium salt, Diadenosine pentaphosphate trilithium salt

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About This Item

Empirical Formula (Hill Notation):
C20H26Li3N10O22P5
CAS Number:
Molecular Weight:
934.17
EC Number:
MDL number:
UNSPSC Code:
12352202
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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

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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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)
Effect of adenosine triphosphate analogues on skeletal muscle fibers in rigor
Schoenberg M
Biophysical Journal, 56(1), 33-41 (1989)

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