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ADP

Basic information Uses Safety Related Supplier
ADP Basic information
  • Product Name:ADP
  • CAS:58-64-0
  • MF:C10H15N5O10P2
  • MW:427.2
  • EINECS:200-392-5
  • Mol File:58-64-0.mol
ADP Chemical Properties
  • Boiling point:196°C
  • Density 2.49±0.1 g/cm3(Predicted)
  • storage temp. -20°C
  • pkapK2: 4.2(-1);pK3: 7.20(-2) (25°C)
  • Merck 13,155
  • BRN 67722
  • InChIKeyXTWYTFMLZFPYCI-KQYNXXCUSA-N
  • EPA Substance Registry SystemAdenosine 5'-(trihydrogen diphosphate) (58-64-0)
Safety Information
  • Safety Statements 24/25
  • WGK Germany 3
  • RTECS AU7467000
  • 10-21
  • HS Code 29349990
MSDS
ADP Usage And Synthesis
  • UsesAdenosine-5'-diphosphate (ADP) is a central component of energy storage, metabolism, and signal transduction in vivo. It serves as a precursor for ATP and, in this capacity, is utilized in a wide number of cellular processes, including respiration, biosynthetic reactions, motility, and cell division.
  • Uses
    Adenosine 5′-diphosphate (5′-ADP or ADP) was used as a test compound for studying the endothelium-dependent vascular response in salt sensitive (DS) and salt resistant Dahl rats (DR). The product was used to study the different P2-purinergic receptor subtypes on canine vascular smooth muscle and endothelium.
  • DefinitionChEBI: A purine ribonucleoside 5'-diphosphate having adenine as the nucleobase.
  • Agricultural UsesAdenosine diphosphate (ADP) is a phosphorus compound formed during the breakdown of adenosine triphosphate (ATP) by dephosphorylation. It is made of adenine, ribose, five carbon sugars and two phosphate groups. ADP acts as a source of energy in biochemical reactions.
  • Biochem/physiol ActionsAdenosine 5′-diphosphate induces human platelet aggregation and non-competitively blocks the stimulated human platelet adenylate cyclase.
  • Enzyme inhibitorThis adenine nucleotide (FWfree-acid = 504.16 g/mol; CAS 58-64-0; Molar Absorptivity = 15,400 M–1cm–1, l = 259 nm) is a product in ATPdependent transphosphorylases, phosphohydrolases, and molecular motors; as such, ADP often inhibits these enzymes. Enzymatic Phosphorylation: ADP is a substrate for adenylate kinase (Reaction: ADP2– + MeADP " MeATP2– + AMP) and other enzymes that stabilize ATP concentrations in prokaryotes [e.g., acetate kinase (Reaction: MgADP + Acetyl-phosphate ! MeATP2– + Acetate)] and eukaryotes [e.g., pyruvate kinase (Reaction: MgADP + Phosphoenolpyruvate ! MgATP2– + Pyruvate), creatine kinase (Reaction: MgADP + Creatine-phosphate ! MgATP2– + Creatine), arginine kinase (Reaction: MgADP + Arginine-phosphate ! MgATP2– + Arginine), and nuclecleotide diphosphate kinase (Reaction: ADP2– + MgGTP2– " MgATP2– + GDP2–)]. ATP Synthase: ADP is a primary substrate for the FOF1 ATP synthase (Reaction: MgADP + Pi + High Chemiosmotic Gradient Energization State ! MgATP2– + Low Chemiosmotic Gradient Energization State). ADP can also become entrapped within a catalytic site of the rotary motor, when proton motive is low, absent, or uncoupled, and its inhibitory action under such conditions is believed to prevent wasteful hydrolysis of ATP (Reaction: MgATP2– + H2O ? MgADP + Pi). Metal Ion Binding Properties: As a polyanion, ADP not only binds physiologic divalent cations Mg2+ and Ca2+, but also forms reversible complexes with Mn2+ and Co2+. For reversible complexation of ADP2– with a metal ion Me2+, (Reaction: ADP2– + Me2+ ! MeADP), Kformation = [MeADP]/[ADP2–]free[Me2+]free, indicating that [MeADP]/[ADP2– ]free = Kformation ′ [Me2+]free. In many cases, metal-free ADP is not a substrate and instead acts as a revesible inhibitor. Good experimental design therefore demands rigorous control of free metal ion concentration to control the ratio of metal-bound and metal-free forms. When exposed to Cr(III) at elevated temperature, ADP also forms ligand exchange-inert complexes with Cr3+. Platelet Aggregation: ADP is also a well-known activator of platelet aggregation, as mediated by the ADP receptors P2Y1, P2Y12 and P2X1. Upon conversion to adenosine by ecto-ADPases, platelet activation is inhibited by means of adenosine receptors. Target(s): Hydrogenomonas facilis ribulosediphosphate (RuDP) carboxylase and NADH-, ATP-dependent CO2 fixation; platelet (Na+/K+)-ATPase; hydrogen-ion transport in chloroplasts; pyruvate dehydrogenase kinase; 5-oxo-L-prolinase, or L-pyroglutamate hydrolase; a-NADHdependent reductase, rat liver microsomes; nitrogenase; Trypanosoma cruzi hexokinase; maize leaf acetyl-coenzyme A carboxylase; rat brain mitochondrial calcium-efflux; sarcoplasmic reticulum Ca2+ ATPase; Na+-Na+ exchange mediated by (Na+/K+)ATPase reconstituted into liposomes; nitrate and nitrite assimilation in Zea mays under dark conditions; PGE1-activated platelet adenylate cyclase in rats and rabbits; mitochondrial F1-ATPase, inactive complex formed upon binding ADP at a catalytic site; ATP-sensitive K+ channels, frog skeletal muscle; human 5-phosphoribosyl-1pyrophosphate synthetase; Crithidia fasciculata glutathionylspermidine synthetase; myosin V ATPase; cystic fibrosis transmembrane conductance regulator (ABC transporter) via its adenylate kinase activity; V type ATPase/synthase.
  • Purification MethodsIt is characterised by conversion to the acridine salt by addition of alcoholic acridine (1.1g in 50mL), filtering off the yellow salt and recrystallising from H2O. The salt has m 215o(dec), max 259nm ( 15,400) in 2O. [Baddiley & Todd J Chem Soc 648 1947, 582 1949, cf LePage Biochemical Preparations 1 1 1949, Martell & Schwarzenbach Helv Chim Acta 39 653 1956]. [Beilstein 26 III/IV 2369.]
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