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A1388

Sigma-Aldrich

Adenosine 5′-[γ-thio]triphosphate tetralithium salt

≥75% (HPLC), powder

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Sinónimos:
ATP-γ-S, Adenosine 5′-(3-thiotriphosphate) tetralithium salt, Ado-5′-PPP[S]
Fórmula empírica (notación de Hill):
C10H12Li4N5O12P3S
Número de CAS:
93839-89-5
Peso molecular:
546.98
Beilstein/REAXYS Number:
6265083
EC Number:
298-862-8
MDL number:
MFCD00077293
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24890536
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

assay

≥75% (HPLC)

form

powder

color

off-white

solubility

H2O: 25 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].[Li+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=S)[C@@H](O)[C@H]3O

InChI

1S/C10H16N5O12P3S.4Li/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(25-10)1-24-28(18,19)26-29(20,21)27-30(22,23)31;;;;/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H,20,21)(H2,11,12,13)(H2,22,23,31);;;;/q;4*+1/p-4/t4-,6-,7-,10-;;;;/m1..../s1

InChI key

DWQFDOIBOYDYKH-KWIZKVQNSA-J

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Application

Adenosine 5′-[γ-thio]triphosphate tetralithium salt has been used to treat the pollen grains to determine the inhibitory effect of adenosine triphosphate (ATP) or its hydrolysis product. It has also been used to select thiophosphorylate target protein.

Biochem/physiol Actions

Adenosine 5′-[γ-thio]triphosphate (ATP-γ-S) is widely used as a non-hydrolyzed ATP analogue for studies on the effects of ATP binding to ATP sites in a wide range of processes including extracellular functions. ATP- γ-S is a P2 purinergic agonist which increases the activity of Ca2+-activated K+ channels. ATP- γ-S can substitute for ATP in kinase reactions yielding thiophosphorylated proteins that are resistant to protein phosphatases and modulate the ATP-dependent steps in the binding of ubiquitin conjugates to the 26S proteasome. ATP-γ -S differentially modulates Toll-like receptor 4-mediated cell survival and death.

Other Notes

Non-hydrolyzable ATP analog

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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S Chrysogelos et al.
The Journal of biological chemistry, 258(20), 12624-12631 (1983-10-25)
recA protein binds to duplex DNA in the presence of Mg2+ and adenosine 5'-O-(3-thiotriphosphate) forming a stiff nucleoprotein filament with a distinct axial repeat which contains 17 +/- 1 base pairs and spans 8-9 nm along the fiber (Di Capua
Andreas Peth et al.
Molecular cell, 40(4), 671-681 (2010-11-26)
Eukaryotic cells target proteins for degradation by the 26S proteasome by attaching a ubiquitin chain. Using a rapid assay, we analyzed the initial binding of ubiquitinated proteins to purified 26S particles as an isolated process at 4°C. Subunits Rpn10 and
David M Smith et al.
Cell, 144(4), 526-538 (2011-02-22)
In the eukaryotic 26S proteasome, the 20S particle is regulated by six AAA ATPase subunits and, in archaea, by a homologous ring complex, PAN. To clarify the role of ATP in proteolysis, we studied how nucleotides bind to PAN. Although
Extracellular ATP is involved in the initiation of pollen germination and tube growth in Picea meyeri
Zhou J, et al.
Trees (Berlin, Germany : West), 29(2), 563-574 (2015)
The enzymatic synthesis of thiophosphate analogs of nucleotides.
R S Goody et al.
Biochimica et biophysica acta, 276(1), 155-161 (1972-07-13)
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