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A4803

Sigma-Aldrich

Adenosine 5′-triphosphate γ-(1-[2-nitrophenyl]ethyl) ester sodium salt

≥95%

Synonym(e):

“Caged” ATP

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About This Item

Empirische Formel (Hill-System):
C18H21N6Na2O15P3
CAS-Nummer:
171800-68-3
Molekulargewicht:
700.29
MDL-Nummer:
MFCD00077294
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24890911

Assay

≥95%

Form

powder

Lagertemp.

−20°C

SMILES String

[Na+].[Na+].CC(OP([O-])(=O)OP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)c4ccccc4[N+]([O-])=O

InChI

1S/C18H23N6O15P3.2Na/c1-9(10-4-2-3-5-11(10)24(27)28)37-41(31,32)39-42(33,34)38-40(29,30)35-6-12-14(25)15(26)18(36-12)23-8-22-13-16(19)20-7-21-17(13)23;;/h2-5,7-9,12,14-15,18,25-26H,6H2,1H3,(H,29,30)(H,31,32)(H,33,34)(H2,19,20,21);;/q;2*+1/p-2/t9?,12-,14-,15-,18-;;/m1../s1

InChIKey

DWGOHIKVVKFGGU-DZHDPEGHSA-L

Anwendung

Adenosine 5′-triphosphate γ-(1-[2-nitrophenyl]ethyl) ester (“Caged” ATP) is used as a photolyzing substrate of luciferase-mediated firefly bioluminescence and other ATP-dependent photolytic processes. Caged ATP has also been used to study the dynamics of ATP-driven linear molecular motors such as myosin Va.

Lagerklassenschlüssel

13 - Non Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

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Katsuyuki Shiroguchi et al.
PLoS biology, 9(4), e1001031-e1001031 (2011-05-03)
Myosins are ATP-driven linear molecular motors that work as cellular force generators, transporters, and force sensors. These functions are driven by large-scale nucleotide-dependent conformational changes, termed "strokes"; the "power stroke" is the force-generating swinging of the myosin light chain-binding "neck"
Takeshi Kageyama et al.
Photochemistry and photobiology, 87(3), 653-658 (2011-01-07)
The reaction process of firefly bioluminescence was studied by photolyzing caged-ATP to adenosine triphosphate (ATP) within 100 ms. The intensity of luminescence increases markedly to reach a maximum within 1 s, maintains almost the same intensity up to 5 s
Christian Völlmecke et al.
The FEBS journal, 276(21), 6172-6186 (2009-09-29)
The mechanism of ATP hydrolysis of a shortened variant of the heavy metal-translocating P-type ATPase CopB of Sulfolobus solfataricus was studied. The catalytic fragment, named CopB-B, comprises the nucleotide binding and phosphorylation domains. We demonstrated stoichiometric high-affinity binding of one
J A McCray et al.
Proceedings of the National Academy of Sciences of the United States of America, 77(12), 7237-7241 (1980-12-01)
2-Nitrobenzyl derivatives have been used for several years as photolabile protecting groups in synthetic organic chemistry. Recently, P3-1-(2-nitro phenylethyladenosine 5'-triphosphate "caged ATP" was synthesized and its photolysis was shown to generate ATP in situ. This and related reactions have great
Savas Tasoglu et al.
Advanced materials (Deerfield Beach, Fla.), 27(26), 3901-3908 (2015-06-11)
A simple, yet powerful magnetic-levitation-based device is reported for real-time, label-free separation, as well as high-resolution monitoring of cell populations based on their unique magnetic and density signatures. This method allows a wide variety of cellular processes to be studied

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