67030-27-7

Basic information

• Product Name: 1-(2-NITROPHENYL)ETHYL ADENOSINE TRIPHOSPHATE
• Synonyms: A-1048;1-(2-NITROPHENYL)ETHYL ADENOSINE TRIPHOSPHATE;CAGED ATP;P(3)-1-(2-nitro)phenylethyladenosine 5'-triphosphate
• CAS NO: 67030-27-7
• Molecular Formula: C₁₈H₂₃N₆O₁₅P₃
• Molecular Weight: 656.327703
• Mol File: 67030-27-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 979.1 °C at 760 mmHg
• Flash Point: 545.9 °C
• Appearance: /
• Density: 2.14 g/cm³
• CAS DataBase Reference: 1-(2-NITROPHENYL)ETHYL ADENOSINE TRIPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-NITROPHENYL)ETHYL ADENOSINE TRIPHOSPHATE(67030-27-7)
• EPA Substance Registry System: 1-(2-NITROPHENYL)ETHYL ADENOSINE TRIPHOSPHATE(67030-27-7)

Safety Data

• Hazardous Substances Data: 67030-27-7(Hazardous Substances Data)

Usage

General Description

1-(2-Nitrophenyl)ethyl adenosine triphosphate is a chemical compound with the formula C22H29N9O15P3. It is a derivative of adenosine triphosphate (ATP) in which the hydroxyl group at the C2' position of the ribose ring is replaced by a 2-nitrophenylethyl moiety. This modification allows for the selective and reversible inhibition of ATP-binding proteins, making it a valuable tool for studying the functions and interactions of various ATP-dependent enzymes. Additionally, the incorporation of the nitrophenyl group allows for detection and tracking of ATP binding and hydrolysis in biological systems, making it useful for biochemical and biophysical studies.

Upstream product

• 577-59-3 2-acetylnitrobenzene 
• 116271-34-2 hydrazone of 2-nitroacetophenone 
• 114119-94-7 1-(2-nitrophenyl)diazoethane 
• 56-65-5 ATP 

Downstream Products

• 25798-61-2 ortho-nitroso acetophenone 
• 56-65-5 ATP 

Relevant articles and documents

Photolabile 1-(2-Nitrophenyl)ethyl Phosphate Esters of Adenine Nucleotide Analogues. Synthesis and Mechanism of Photolysis

A general method is described for preparing photolabile 1-(2-nitrophenyl)ethyl esters of phosphate and thiophosphate compounds.The method is based on selective alkylation of weakly ionizing phosphate groups by a new alkylating agent, 1-(2-nitrophenyl)diazoethane.ATP and the widely used structural analogues of ATP, 5'-adenylyl imidodiphosphate (ATP(β,γNH)) and adenosine 5'-(3-thiophsophate) (ATP(γS)), were alkylated on the terminal (γ) phosphate group.ATP(γS) was alkylated on oxygen or on sulfur in approximately equal amounts.Photolysis of P3-1-(2-nitrophenyl)ethyladenosine 5'-triphosphate, commonly called "caged ATP", was analyzed spectroscopically at pH values close to neutral in aqueous solvents by use of laser pulse photolysis.The kinetics of formation of the three products, ATP, 2-nitrosoacetophenone, and H+, were each monitored, as well as the kinetics of formation and decay of an intermediate presumed to be an aci-nitro compound (apparent ε406nm = 9.1 x 103 M-1 cm-1).For caged ATP in the presence of 3 mM MgCl2, and aci-nitro intermediate and H+ formed first at > 105 s-1 followed by the decay of the intermediate at 86 s-1 at pH 7.1, 21 deg C, and ionic strength 0.18 M.ATP, monitored by a biochemical assay, and 2-nitrosoacetophenone, monitored by a characteristic absorption band at 740 nm, were formed simultaneously with the decay of the intermediate under all conditions tested.The rate of decay of the aci-nitro intermediate was therefore used as a measure of the rate of release of the nucleotide analogues from their photolabile precursors.At pH 7.1, 0.18 M ionic strength, and 21 deg C the rate constants ranged from 35 to 250 s-1 and displayed a similar dependence on pH as caged ATP.The steady-state quantum yields of the 1-(2-nitrophenyl)ethyl phosphate esters were in the range 0.49 - 0.63.The deleterious effect of 2-nitrosoacetophenone on biological materials can be avoided by having thiols present.The reaction kinetics of dithiothreitol and 2-nitrosoacetophenone was described by a two-step process, the first step having a rate constant of 3.5 x 103 M-1 s-1 and the second 45 s-1 at pH 7.0, 21 deg C, and ionic strength 0.18 M.