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A1388

Sigma-Aldrich

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

≥75% (HPLC), synthetic (organic), powder

Synonym(s):

ATP-γ-S, Adenosine 5′-(3-thiotriphosphate) tetralithium salt, Ado-5′-PPP[S]

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About This Item

Empirical Formula (Hill Notation):
C10H12Li4N5O12P3S
CAS Number:
93839-89-5
Molecular Weight:
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

Key Documents

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Product Name

Adenosine 5′-[γ-thio]triphosphate tetralithium salt, ≥75% (HPLC), powder

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
SLCJ3618
SLCG1400
SLCD6481
SLCB8192
SLBZ2052

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Labeling and identification of direct kinase substrates
Carlson SM and White FM
Science Signaling, 5(227), pl3-pl3 (2012)
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
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
Kana Harada et al.
Journal of neurochemistry, 116(6), 1138-1147 (2011-01-08)
The survival and death rates of inflammatory cells directly control their number and are substantially associated with the degree of inflammation. Microglia, key players in neuroinflammation, often cause excessive reactions implicated in neurological diseases. However, the mechanisms that determine microglial
Tsui-Fen Chou et al.
Journal of molecular biology, 426(15), 2886-2899 (2014-06-01)
The p97 AAA (ATPase associated with diverse cellular activities), also called VCP (valosin-containing protein), is an important therapeutic target for cancer and neurodegenerative diseases. p97 forms a hexamer composed of two AAA domains (D1 and D2) that form two stacked
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