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N6-Propargyl-ATP (N6pATP)

N6-Propargyl-adenosine-5'-triphosphate, Sodium salt

Cat. No. Amount Price (EUR) Buy / Note
CLK-NU-001-1 1 mg 107,66 Add to Basket/Quote Add to Notepad
CLK-NU-001-5 5 mg 431,21 Add to Basket/Quote Add to Notepad
Structural formula of N6-Propargyl-ATP (N6pATP) (N6-Propargyl-adenosine-5'-triphosphate, Sodium salt)
Structural formula of N6-Propargyl-ATP (N6pATP)

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)

Applications:
in vitro AMPylation of proteins[1,2]
in vitro polyadenylation of RNA[3]
The resulting alkyne-functionalized protein[1,2] or RNA[3] can subsequently be processed via Cu(I)-catalyzed (azide-alkyne) click chemistry that offers the choice

  • to introduce a Biotin group for subsequent purification tasks (via Azides of Biotin)
  • to introduce fluorescent group for subsequent microscopic imaging (via Azides of fluorescent dyes)
  • to crosslink the RNA to azide-functionalized biomolecules e.g.proteins
Presolski et al.[4] and Hong et al.[5] provide a general protocol for Cu(I)-catalyzed click chemistry reactions that may be used as a starting point for the set up and optimization of individual assays.
Agonistic ligand, mainly for nucleoside receptor A1
Nucleoside-triphosphates can be converted by different membrane-bound phosphatases into nucleosides acting as nucleoside receptor ligands. In some cases nucleoside phosphates act also directly on nucleoside receptors.

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.

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Product Citations:
Please click the black arrow on the right to expand the citation list. Click publication title for the full text.

Selected References:
[1] Grammel et al. (2011) A Chemical Reporter for Protein AMPylation. J. Am. Chem. Soc. 133:17103.
[2] Broncel et al. (2012) A New Chemical Handle for Protein AMPylation at the Host-Pathogen Interface. ChemBioChem 13:183.
[3] Grammel et al. (2012) Chemical Reporter for Monitoring RNA Synthesis and Poly (A) Tail Dynamics. ChemBioChem 13:1112.
[4] Presolski et al. (2011) Copper-Catalyzed Azide-Alkyne Click Chemistry for Bioconjugation. Current Protocols in Chemical Biology 3:153.
[5] 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.