N6-Propargyl-adenosine-5'-triphosphate, Sodium salt
For research use only!
Shipping: shipped on blue ice
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: C13H18N5O13P3 (free acid)
Molecular Weight: 545.23 g/mol (free acid)
Exact Mass: 545.01 g/mol (free acid)
Purity: ≥ 95 % (HPLC)
Form: white to off-white solid
Solubility: 10 mM Tris-HCl pH 7.5
Spectroscopic Properties: λmax 262 nm, ε 18.0 L mmol-1 cm-1 (Tris-HCl pH 7.5)
in vitro AMPylation of proteins[1,2]
in vitro polyadenylation of RNA
The resulting alkyne-functionalized protein[1,2] or RNA can subsequently be processed via Cu(I)-catalyzed (azide-alkyne) click chemistry that offers the choice
Please note: This compound contains a phosphoramide linkage which is hydrolyzed at pH <7.0.
For preparation of a 10 mM solution use 100 mM buffer (for example: bicarbonate, borate, phosphate and Tris) to prevent degradation at acidic pH.
Please click the black arrow on the right to expand the citation list. Click publication title for the full text.
 Grammel et al. (2011) A Chemical Reporter for Protein AMPylation. J. Am. Chem. Soc. 133:17103.
 Broncel et al. (2012) A New Chemical Handle for Protein AMPylation at the Host-Pathogen Interface. ChemBioChem 13:183.
 Grammel et al. (2012) Chemical Reporter for Monitoring RNA Synthesis and Poly (A) Tail Dynamics. ChemBioChem 13:1112.
 Presolski et al. (2011) Copper-Catalyzed Azide-Alkyne Click Chemistry for Bioconjugation. Current Protocols in Chemical Biology 3:153.
 Hong et al. (2011) Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation. Angew. Chem. Int. Ed. 48:9879.
Sirci et al. (2012) Ligand-, structure- and pharmacophore-based molecular fingerprints: a case study on adenosine A1, A2A, A2B, and A3 receptor antagonists. J. Comput. Aided Mol. Des. 26:1247.
Volonte et al. (2009) Membrane components and purinergic signalling: the purinome, a complex interplay among ligands, degrading enzymes, receptors and transporters. FEBS J. 276:318.
Yegutkin (2008) Nucleotide and nucleoside converting enzymes: Important modulators of purinergic signalling cascade. Biochim. Biophys. Acta 1783:673.
Joshi et al. (2005) Purine derivatives as ligands for A3 adenosine receptors. Current Topics in Medicinal Chemistry 5:1275.
Volpini et al. (2002) N6-Alkyl-2-alkynyl derivatives of adenosine as potent and selective agonists of the human adenosine A3 receptor and starting point for searching A2B ligands. J. Med. Chem. 45 (15):3271.
Hess (2001) Recent advantages in adenosine receptor antagonist research. Expert Opin. Ther. Patents 11 (10):1533.
Jacobson (2001) Probing adenosine and P2 receptors: design of novel purines and nonpurines as selective ligands. Drug Development Res. 52:178.
Jacobson et al. (2001) Ribose modified nucleosides and nucleotides as ligands for purine receptors. Nucleosides, Nucleotides & Nucleic Acids 20 (4):333.
Van Galen et al. (1994) A binding site model and structure-activity relationships for rat A3 adenosine receptor. Molecular Pharmacology 45:1101.