188
Views
1
CrossRef citations to date
0
Altmetric
Original Articles

Concise and Efficient Synthesis of 3′-O-Tetraphosphates of 2′-Deoxyadenosine and 2′-Deoxycytidine

, , &
Pages 33-39 | Received 28 Apr 2014, Accepted 07 Aug 2014, Published online: 16 Dec 2014

REFERENCES

  • Desaubry, L.; Shoshani, I.; Johnson, R.A. Inhibition of adenylyl cyclase by a family of newly synthesized adenine nucleoside 3′-polyphosphates. J. Biol. Chem. 1996, 271, 14028–14034.
  • Johnson, R.A.; Desaubry, L.; Bianchi, G.; Shoshani, I.; Lyons, E. Jr.; Taussig, R.; Watson, P.A.; Cali, J.J.; Krupinski, J.; Pieroni, P.A.; Iyengar, R. Isozyme-dependent sensitivity of adenylyl cyclases to P-site-mediated inhibition by adenine nucleosides and nucleoside 3′-polyphosphates. J. Biol. Chem. 1997, 272, 8962–8966.
  • Beavo, J.A. Cyclic nucleotide phosphodiesterases: functional implications of multiple isoforms. Physiol. Rev. 1995, 75, 725–748.
  • Londos, C.; Wolf, J. Two distinct adenosine-sensitive sites on adenylate cyclase. Proc. Natl. Acad. Sci. USA 1977, 74, 5482–5486.
  • Johnson, R.A.; Yeung, S.-M.H.; Stubner, D.; Bushfield, M.; Shoshani, I. Cation and structural requirements for P site-mediated inhibition of adenylate cyclase. Mol. Pharmacol. 1989, 35, 681–688.
  • Desaubry, L.; Shoshani, I.; Johnson, R.A. 2′,5′-dideoxyadenosine 3′-polyphosphates are potent inhibitors of adenylyl cyclases. J. Biol. Chem. 1996, 271, 2380–2382.
  • Desaubry, L.; Shoshani, I.; Johnson, R.A. J. Biol. Chem. 1996, 271, 14028–14034.
  • Scoechtig, E.; Trost, T. Inhibition of adenylyl cyclase by a family of newly synthesized adenine nucleoside 3′-polyphosphates. Pharmacology 1981, 23, 82–90.
  • Desaubry, L.; Johnson, R.A. Adenosine nucleoside 3′-tetraphoaphates are novel and potent inhibitors of adenylyl cyclases. J. Biol. Chem. 1998, 273, 24972–24977.
  • De Souza, N.J. Industrial development of traditional drugs: the forskolin example. A mini-review. J. Ethnopharmacol. 1993, 38, 177–180.
  • Kumar, S.; Sood, A.; Wegener, J.; Finn, P.J.; Nampalli, S.; Nelson, J.R.; Sekher, A.; Mitsis, P.; Macklin, J.; Fuller, C.W. Terminal phosphate labeled nucleotides: Synthesis, applications, and linker effect on incorporation by DNA polymerases. Nucleos. Nucleot. Nucl. Acids 2005, 24, 401–408.
  • Korlach, J.; Bibillo, A.; Wegener, J.; Peluso, P.; Pham, T.T.; Park, I.; Clark, S.; Otto, G.A.; Turner, S.W. Long, processive enzymatic DNA synthesis using 100% dye-labeled terminal phosphate-linked nucleotides. Nucleos. Nucleot. Nucl. Acids 2008, 27, 1072–1082.
  • Kore, A.R.; Yang, B.; Srinivasan, B. Concise and efficient synthesis of 3′-O-triphosphates of 2′-deoxyadenosine and 2′-deoxycytidine. Tetrahedron Lett. 2014, 55, 1573–1576.
  • Kore, A.R.; Shanmugasundaram, M.; Senthilvelan, A.; Srinivasan, B. An improved protection-free one-pot chemical synthesis of 2′-deoxynucleoside-5′-triphosphates. Nucleos. Nucleot. Nucl. Acids 2012, 31(5), 423–431.
  • Kore, A.R.; Shanmugasundaram, M.; Senthilvelan, A.; Srinivasan, B. Gram-scale chemical synthesis of 2′-deoxynucleoside-5′-triphosphates. Curr. Protocols Nuc. Acid Chem. 2012, 13.10.1113.10.12.
  • Kore, A.R.; Senthilvelan, A.; Srinivasan, B.; Shanmugasundaram, M. Facile protection-free one-pot chemical synthesis of nucleoside-5′-tetraphosphates. Nucleos. Nucleot. Nucl. Acids 2013, 32, 411–420.
  • Kore, A.R.; Senthilvelan, A.; Shanmugasundaram, M. A new, facile, and protection-free one-pot chemical synthesis of 2′-deoxynucleoside-5′-tetraphosphates. Tetrahedron Lett., 2012, 53, 5868–5870.
  • Kore, A.R.; Yang, B.; Srinivasan, B. Concise synthesis of 5-methyl-, 5-formyl, and 5-carboxy analogues of 2′-deoxycytidine-5′-triphosphate. Tetrahedron Lett. 2013, 54, 5325–5327.
  • Kore, A.R.; Yang, B.; Srinivasan, B. Fluorous-assisted synthesis of (E)-5-[3-Aminoallyl]-uridine-5′-triphosphate. Tetrahedron Lett. 2013, 54, 6264–6266.
  • Kore, A.R.; Senthilvelan, A.; Srinivasan, B.; Shanmugasundaram, M. Facile protection-free one-pot synthesis of 7-deaza-2′-deoxyguanosine-5′-triphosphate - A versatile molecular biology probe. Can. J. Chem. 2013, 91, 718–720.
  • Kore, A.R.; Srinivasan, B. Recent advances in the syntheses of nucleoside triphosphates. Curr. Org. Synth. 2013, 10(6), 903–934.
  • Kore, A.R.; Srinivasan, B. Efficient synthesis of 3-cyanovinylcarbazole-1′-β-deoxyriboside-5′-triphosphate: a reversible photo-cross-linking probe. Tetrahedron Lett., 2012, 53, 4012–4014.
  • Kore, A.R.; Shanmugasundaram, M. Highly stereoselective palladium-catalyzed Heck coupling of 5-iodouridine-5′-triphosphates with allylamine: a new efficient method for the synthesis of (E)-5-aminoallyl-uridine-5′-triphosphates. Tetrahedron Lett., 2012, 53, 2530–2532.
  • Kore, A.R.; Senthilvelan, A.; Shanmugasundaram, M. Highly chemoselective palladium-catalyzed Sonogashira coupling of 5-iodouridine-5′-triphosphates with propargylamine: a new efficient method for the synthesis of 5-aminopropargyl-uridine-5′-triphosphates. Tetrahedron Lett., 2012, 53, 3070–3072.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.