Simple Synthesis of P¹P²-Diadenosine 5′-Pyrophosphate

REFERENCES

• Delicado , E. G. ; Miras-Portugal , M. T. ; Carrasquero , L. M. ; Leon , D. ; Perez-Sen , R. ; Gualix , J. Dinucleoside polyphosphates and their interaction with other nucleotide signalling pathways . Pflugers Arch . 2006 , 452 , 563 – 572 .
   PubMed Web of Science ®Google Scholar
• Stavrou , B. M. Diadenosine polyphosphates: postulated mechanisms mediating the cardiac effects . Curr. Med. Chem. Cardiovasc. Hematol. Agents 2003 , 1 , 151 – 169 .
   PubMedGoogle Scholar
• Jankowski , J. ; Hagemann , J. ; Tepel , M. ; van Der Giet , M. ; Stephan , N. ; Henning , L. ; Gouni-Berthold , I. ; Sachinidis , A. ; Zidek , W. ; Schluter , H. Dinucleotides as growth-promoting extracellular mediators: Presence of dinucleoside diphosphates Ap2A, Ap2G, and Gp2G in releasable granules of platelets . J. Biol. Chem . 2001 , 276 ( 12 ), 20804 – 20809 .
   Web of Science ®Google Scholar
• Basile , G. ; Taglialatela-Scafati , O. ; Damonte , G. ; Armirotti , A. ; Bruzzone , S. ; Guida , L. ; Franco , L. ; Usai , C. ; Fattorusso , E. ; De Flora , A. ; Zocchi , E. ADP-ribosyl cyclases generate two unusual adenine homodinucleotides with cytotoxic activity on mammalian cells . Proc. Natl. Acad. Sci. USA 2005 , 102 , 14509 – 14514 .
   PubMed Web of Science ®Google Scholar
• Khorana , H. G. Carbodiimides, part V: A novel synthesis of adenosine di- and triphosphate and P1,P2-diadenosine-5′-pyrophosphate . J. Am. Chem. Soc . 1954 , 76 , 3517 – 3522 .
   Google Scholar
• Christie , S. M. H. ; Elmore , D. T. ; Kenner , G. W. ; Todd , A. R. ; Weymouth , F. J. Nucleotides, part XXII: Syntheses of P1P2-diadenosine-5 and P1P2-diuridine-5 pyrophosphates . J. Chem. Soc. London 1953 , 2947 – 2953 .
   Google Scholar
• Moffatt , J. G. ; Khorana , H. G. Nucleoside Polyphosphates, VIII: New and improved syntheses of uridine diphosphate glucose and flavin adenine dinucleotide using nucleoside-5′ phosphoramidates . J. Am. Chem. Soc . 1958 , 80 , 3756 – 3761 .
   Web of Science ®Google Scholar
• Shimazu , M. ; Shinozuka , K. ; Sawai , H. Facile synthesis of nucleotides containing polyphosphates by Mn (II) and Cd (II) ion-catalyzed pyrophosphate bond formation in aqueous solution. Tetrahedron Lett . 1990, 31, 235–238.
   Web of Science ®Google Scholar
• Kanavarioti , A. ; Lu , J. ; Rosenbach , M. T. ; Hurley , T. B. Unexpectedly facile synthesis of symmetrical P1,P2-dinucleoside-5′pyrophosphates . Tetrahedron Lett. 1991 , 32 , 6065 – 6068 .
   PubMed Web of Science ®Google Scholar
• Shabarova , Z. A. Chemical development in the design of oligonucleotide probes for binding to DNA and RNA . Biochimie 1988 , 70 , 1323 – 1334 .
   PubMed Web of Science ®Google Scholar
• Ng , K. E. ; Orgel , L. E. The action of a water-soluble carbodiimide on adenosine-5′-polyphosphates . Nucleic Acids Res . 1987 , 15 , 3573 – 3580 .
   PubMed Web of Science ®Google Scholar
• Jankowsky , J. ; Potthoff , W. ; Zidek , W. ; Schluter , H. Purification of chemically synthesised dinucleoside (5′,5′) polyphosphates by displacement chromatography . J. Chromatogr. B 1998 , 719 , 63 – 70 .
   PubMed Web of Science ®Google Scholar
• Moffatt , J. G. ; Khorana , H. G. Nucleoside polyphosphates, X: The synthesis and some reactions of nucleoside-5′ phosphoromorpholidates and related compounds: Improved methods for the preparation of nucleoside-5′ polyphosphates . J. Am. Chem. Soc . 1961 , 83 , 649 – 658 .
   Web of Science ®Google Scholar
• Rossi , L. ; Brandi , G. ; Schiavano , G. F. ; Balestra , E. ; Millo , E. ; Scarfì , S. ; Damonte , G. ; Gasparini , A. ; Magnani , M. ; Perno , C. F. ; Benatti , U. ; De Flora A. Macrophage protection against human immunodeficiency virus or herpes simplex virus by red blood cell-mediated delivery of a heterodinucleotide of azidothymidine and acyclovir . AIDS Res. and Hum. Retroviruses 1998 , 14 , 435 – 444 .
   PubMed Web of Science ®Google Scholar
• Rajbhandary , U. L. ; Young , R. J. ; Khorana , H. G. Studies on polynucleotides, xxxii: The labelling of end groups in polynucleotide chains: the selective phosphorylation of phosphomonoester groups in amino acid acceptor ribonucleic acids . J. Biol. Chem . 1964 , 239 , 3875 – 3884 .
   PubMed Web of Science ®Google Scholar
• Bruzzone , S. ; Dodoni , G. ; Kaludercic , N. ; Basile , G. ; Millo , E. ; De Flora , A. ; Di Lisa , F. ; Zocchi , E. Mitochondrial dysfunction induced by a cytotoxic adenine dinucleotide produced by ADP-ribosyl cyclases from cADPR . J. Biol. Chem . 2007 , 282 , 5045 – 5052 .
   PubMed Web of Science ®Google Scholar
• Goldman , L. ; Marsico , J. W. ; Anderson , G. W. The preparation of adenosine-5′-imidazol-1-ylphosphonate and its reactions with nucleophiles: A novel synthesis of nucleotide coenzymes . J. Am. Chem. Soc . 1960 , 82 , 2969 – 2970 .
   Google Scholar