Adenosine-5'-[(β,γ)-methyleno]triphosphate, Sodium salt
For general laboratory use.
Shipping: shipped on gel packs
Storage Conditions: store at -20 °C
Short term exposure (up to 1 week cumulative) to ambient temperature possible.
Shelf Life: 12 months after date of delivery
Molecular Formula: C11H18N5O12P3 (free acid)
Molecular Weight: 505.21 g/mol (free acid)
Exact Mass: 505.02 g/mol (free acid)
Purity: ≥ 95 % (HPLC)
Color: white to off-white
Spectroscopic Properties: λmax 259 nm, ε 15.4 L mmol-1 cm-1 (Tris-HCl pH 7.5)
Conformational studies on complex with mevalonate diphosphate decarboxylase
Structure of the complex with folylpolyglutamate synthetase
Structure of complex with p90 ribosomal S6 kinases
Crystal structure of complex with Ca2+-ATPase
NMR-studies of complex with yeast hexokinase
Agonistic ligand, mainly for nucleoside receptor A1
Nucleosidephosphates stabilized against hydrolytic degradation can directly bind to nucleoside receptors.
Nonhydrolyzable ligand for P2X purinoreceptor[7,8]
BIOZ Product Citations:
 Reuther et al. (2011) Backbone 1H, 13C, 15N NMR assignments of the unliganded and substrate ternary complex forms of mevalonate diphosphate decarboxylase from Streptococcus pneumoniae. Biomol. NMR Assign. 5 (1):11.
 Young et al. (2008) Structures of Mycobacterium tuberculosis folylpolyglutamate synthase complexed with ADP and AMPPCP. Acta Crystallogr D Biol Crystallogr. D64 (Pt 7):745.
 Ikuta et al. (2007) Crystal structures of the N-terminal kinase domain of human RSK1 bound to three different ligands: Implications for the design of RSK1 specific inhibitors. Protein Sci. 16 (12):2626.
 Picard et al. (2005) The average conformation at micromolar [Ca2+] of Ca2+-atpase with bound nucleotide differs from that adopted with the transition state analog ADP.AlFx or with AMPPCP under crystallization conditions at millimolar [Ca2+]. J. Biol. Chem. 280 (19):18745.
 Maity et al. (2002) Structure of triphosphoryl nucleotide bound at the active site of yeast hexokinase: 1H-nuclear magnetic resonance study. J. Protein Chem. 21 (4):265.
 Kubala (2006) ATP-binding to P-type ATPases as revealed by biochemical, spectroscopic, and crystallographic experiments. Proteins. 64 (1):1.
 Trezise et al. (1995) The selective P2X purinoceptor agonist, beta,gamma-methylene-L-adenosine 5'-triphosphate, discriminates between smooth muscle and neuronal P2X purinoceptors. Arch. Pharmacol. 351 (6):603.
O'Connor et al. (1990) Characterization of P2x-receptors in rabbit isolated ear artery. Br. J. Pharmacol. 101 (3):640.
Del Toro Duany et al. (2008) The reverse gyrase helicase-like domain is a nucleotide-dependent switch that is attenuated by the topoisomerase domain. Nucleic Acids Research 36 (18):5882.
Toyoshima et al. (2004) Crystal structure of the calcium pump with a bound ATP analogue. Nature 430:529.
Mayer et al. (1991) Re-evaluation of the specificity of adenylyl (beta,gamma-methylene)diphosphonate as a substrate for adenylate cyclase. Histochem J. 23 (2):100.
Williams et al. (1986) Effects of purine nucleotides on the binding of [3H]cyclopentyladenosine to adenosine A1-receptors in rat brain membranes. J. Neurochem. 47 (1):88.
Mayer et al. (1985) Specificity of cytochemical demonstration of adenylate cyclase in liver using adenylate- (beta, gammamethylene) diphosphate as substrate. Histochemistry. 82 (2):135.
Meghji et al. (1984) The effect of adenylyl compounds on the heart of the dogfish, Scyliorhinus canicula. Comparative Biochem. and Physiol.Part C: Pharmacol., Toxicol.& Endocrin. 77C (2):295.
Meghji et al. (1983) The effect of adenylyl compounds on the heart of the axolotl (Ambystema mexicanum). Comparative Biochem. and Physiol.Part C: Pharmacol., Toxicol.& Endocrin. 76 (2):319.