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ara-cAMP

Arabinoadenosine- 3', 5'- cyclic monophosphate ( ara-cAMP ), sodium salt
Inactive form of the second messenger cyclic AMP
Cat. No.: A 076
    
CAS No.: [32465-18-2]
Shipping: ambient
Product Name Price (net) Qty
Cat. No.: A 076-05
Unit: 5 µmol / ~1.8 mg
$173.00
For other salt forms please inquire. Analogue of the second messenger cyclic AMP with an inverted configuration at the 2’- hydroxy group. Useful for receptor mapping studies and negative controls. Detailed technical information available. Reference: Miller, Adv. Cyclic Nucleot. Res.,14, 335 – 344 (1981); Jäger et al., J. Biol. Chem., 87, 1210 - 1219 (2012).
Cat. No. A 076
CAS number [32465-18-2]
Purity > 98% HPLC
Salt form Sodium
Storage temperature -20°C / -4°F
Molecular formula C₁₀H₁₁N₅O₆P·Na
Molecular weight [g/mol] 351,2
Modifications 2'-cAMP
Lipophilicity 0.99
Absorption max [nm] 259
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 15000
  • 1. Jäger R., Russwurm C., Schwede F., Genieser H.-G., Koesling D.Russwurm M., J. Biol. Chem., 287, 1210 - 1219 (2012), "Activation of PDE10 and PDE11 Phosphodiesterases"
  • 2. Morr M., Ernst L.Mengel R., Liebigs Annalen der Chemie, 4, 651 - 665 (1982), "Some Derivatives of the 3',5'-cyclophosphates of Adenosine"
  • 3. Miller J. P., Adv. Cyclic Nucl. Res., 14, 335 - 344 (1981), "Cyclic AMP Derivatives as Tools for Mapping Cyclic AMP Binding Sites of Cyclic AMP-dependent Protein Kinases I and II"
  • 4. Yagura T. S.Miller J. P., Biochemistry, 20, 879 - 887 (1981), "Mapping Adenosine Cyclic 3',5'- Phosphate Binding Sites on Type I and Type II Adenosine Cyclic 3',5'- Phosphate Dependent Protein Kinases Using Ribose Ring and Cyclic Phosphate Ring Analogues of Adenosine Cyclic 3', 5'- Phosphate"
  • 5. Khwaja T. A., Boswell K. H., Robins R. K.Miller J. P., Biochemistry, 14, 4238 - 4244 (1975), "8-Substituted Derivatives of Adenosine 3', 5'- Cyclic Phosphate Require an Unsubstituted 2'- Hydroxyl Group in the Ribo Configuration for Biological Activity"
  • 6. Plunkett W.Cohen S. S., Cancer Res., 35, 1547 - 1554 (1975), "Two Approaches that Increase the Activity of Analogs of Adenine Nucleosides in Animal Cells"
  • 7. Revankar G. R., Huffman J. H., Allen L. B., Sidwell R. W., Robins R. K.Tolman R. L., J. Med. Chem., 18, 721 - 726 (1975), "Synthesis and Antiviral Activity of Certain 5'-monophosphates of 9-D-arabinofuranosyladenosine and 9-D-arabinofuranosylhypoxanthine"
  • 8. Krakow J. S., BBA Nucleic Acid. Prot. Synthesis, 383, 345 - 350 (1975), "Adenosine Cyclic Monophosphate Receptor. Effect on cyclic AMP Analog on DNA Binding and Protoeolytic Inactivation"
  • 9. Mian A. M., Harris R., Sidwell R. W., Robins R. K.Khwaja T. A., J. Med. Chem., 17, 259 - 2663 (1974), "Synthesis and Biological Activity of 9-β-D- Arabinofuranosyladenine Cyclic 3', 5'- Phosphate and 9-β-D- Arabinofuranosylguanine Cyclic 3', 5'- Phosphate"
  • 10. Anderson W. B., Perlman R. L.Pastan I., J. Biol. Chem., 247, 2717 - 2722 (1972), "Effect of Adenosine 3', 5'- Monophosphate Analogues on the Activity of the Cyclic Adenosine 3', 5'- Monophosphate Receptor in Escherichia coli"
  • 11. LePage G. A.Hersh E. M., Biochem. Biophys. Res. Commun., 46, 1918 - 1922 (1972), "Cyclic Nucleotide Analogs as Carcinostatic Agents"
  • 12. Schweizer M. P.Robins R. K., Conform. Biol. Mol. Polym., 0, 329 - 343 (1972), "NMR Studies on the Conformation of Nucleosides and 3',5'-cyclic Nucleotides"
  • 13. Hughes R. G., Diss. Abstr. Int. B 1973, 33, 4684 - 0 (1972), "Biochemical Effects of cyclic-Ara-cAMP and Rhodium(II) Acetate in L1210 Cells"
  • 14. Hughes R. G.Kimball A. P., Cancer Res., 32, 1791 - 1794 (1972), "Metabolic Effects of cyclic 9-beta-D-arabinofuranosyladenine 3',5'-monophosphate in L1210 Cells"
  • 15. Lee W. W., Fisher L. V.Goodman L., J. Heterocycl. Chem., 8, 179 - 180 (1971), "9-(Beta-D-Arabinofuranosyl)adenine 3',5'-Cyclic Phosphate"