α, β-Methylene ADP
Catalog #:
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Synonyms: Adenosine 5'-(α, β-methylene)diphosphate , ADP[α, β-CH2], AMP-CP

IUPAC Name:
α, β-Methyleneadenosine 5'-diphosphate
Functional Activity:
Selective inhibitor of Ecto-5'-nucleotidase (CD73), a central surface enzyme that generates extracellular adenosine. It is therefore used to study adenosine activity.
Technical Data:
M.Wt: 425.23
Formula: C11H17N5O9 P2
Solubility: Soluble in DMSO
Purity: >99%
Storage: Dessicate at -20°C
CAS No.: 3768-14-7
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References for α,β-Methylene ADP
1. Zhu, G. D., Gandhi, V. B., Gong, J., Thomas, S., Luo, Y., Liu, X., Shi, Y., Klinghofer, V., Johnson, E. F., Frost, D., Donawho, C., Jarvis, K., Bouska, J., Marsh, K. C., Rosenberg, S. H., Giranda, V. L., and Penning, T. D. Synthesis and SAR of novel, potent and orally bioavailable benzimidazole inhibitors of poly(ADP-ribose) polymerase (PARP) with a quaternary methylene-amino substituent. Bioorg Med Chem Lett, 18: 3955-3958, 2008.
2. Dixon, C. J., Cobbold, P. H., and Green, A. K. Adenosine 5'-[alpha beta-methylene]triphosphate potentiates the oscillatory cytosolic Ca2+ responses of hepatocytes to ATP, but not to ADP. Biochem J, 293 ( Pt 3): 757-760, 1993.
3. Breaker, R. R., Gough, G. R., and Gilham, P. T. Polynucleotide phosphorylase forms polymers from an ADP analog in which the 5' oxygen is replaced by a methylene group. Nucleic Acids Res, 18: 3085-3086, 1990.
4. Bertrand, G., Gross, R., Chapal, J., and Loubatieres-Mariani, M. M. [Potentiating synergism between alpha, beta-methylene ADP and acetylcholine on the secretion of insulin from the isolated pancreas of the newborn dog]. C R Seances Soc Biol Fil, 181: 35-39, 1987.
5. Milner-White, E. J. and Rycroft, D. S. The alpha beta-methylene analogues of ADP and ATP act as substrates for creatine kinase. delta G0 for this reaction and for the hydrolysis of the alpha beta-methylene analogue of ATP. Eur J Biochem, 133: 169-172, 1983.
6. Jain, J. C. and Horak, A. Interaction of a methylene diphosphonate analog of ADP with photosynthetic membranes of chloroplasts. Biochem Biophys Res Commun, 97: 166-172, 1980.