Citation: Qi Sun, Jian Sun, Shan-Shan Gong, Cheng-Jun Wang, Xing-Cong Wang. Synthesis of nucleoside tetraphosphates and dinucleoside pentaphosphates from nucleoside phosphoropiperidates via the activation of P(V)-N bond[J]. Chinese Chemical Letters, ;2015, 26(1): 89-92. doi: 10.1016/j.cclet.2014.09.015 shu

Synthesis of nucleoside tetraphosphates and dinucleoside pentaphosphates from nucleoside phosphoropiperidates via the activation of P(V)-N bond

  • Corresponding author: Qi Sun, 
  • Received Date: 12 June 2014
    Available Online: 11 September 2014

    Fund Project: Scientific Research Foundation of Chinese Ministry of Human Resources and Social Security for Returned Chinese Scholars (2011) (No. 212092)Startup Funds for PhDs (2010) from JXSTNU for financial support. (2011)

  • A novel and efficient method for the preparation of nucleoside 50-tetraphosphates has been developed by coupling nucleoside 5'-phosphoropiperidates with triphosphate reagent in the presence of 4, 5-dicyanoimidazole (DCI) activator. Further coupling of the nucleoside 5'-tetraphosphates with nucleoside 50-phosphoropiperidates via the P(V)-N activation strategy provided a reliable synthetic method for both symmetrical and asymmetrical dinucleoside pentaphosphates.
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    1. [1]

      [1] (a) V. Jankowski, M. van der Giet, H. Mischak, et al., Dinucleoside polyphosphates: strong endogenous agonists of the purinergic system, Br. J. Pharmacol. 157 (2009) 1142-1153;

    2. [2]

      (b) E.G. Delicado, M.T. Miras-Portugal, L.M. Carrasquero, et al., Dinucleoside polyphosphates and their interaction with other nucleotide signaling pathways, Pflugers Arch. 452 (2006) 563-572.

    3. [3]

      [2] (a) H. Schlüter, E. Offers, G. Brüggemann, et al., Diadenosine phosphates and the physiological control of blood pressure, Nature 367 (1994) 186-188;

    4. [4]

      (b) M. van der Giet, S. Schmidt, M. Tölle, et al., Effects of dinucleoside polyphosphates on regulation of coronary vascular tone, Eur. J. Pharmacol. 448 (2002) 207-213;

    5. [5]

      (c) V. Jankowski, S. Karadogan, R. Vanholder, et al., Paracrine stimulation of vascular smooth muscle proliferation by diadenosine polyphosphates released from proximal tubule epithelial cells, Kidney Int. 71 (2007) 994-1000.

    6. [6]

      [3] M. van der Giet, T. Westhoff, O. Cinkilic, et al., The critical role of adenosine and guanosine in the affinity of dinucleoside polyphosphates to P(2X)-receptors in the isolated perfused rat kidney, Br. J. Pharmacol. 132 (2001) 467-474.

    7. [7]

      [4] J. Jankowski, V. Jankowski, B. Seibt, et al., Identification of dinucleoside polyphosphates in adrenal glands, Biochem. Biophys. Res. Commun. 304 (2003) 365-370.

    8. [8]

      [5] (a) N. Stern, D.T. Major, H.E. Gottlieb, et al., What is the conformation of physiologically active dinucleoside polyphosphates in solution? Conformational analysis of free dinucleoside polyphosphates by NMR and molecular dynamics simulations, Org. Biomol. Chem. 8 (2010) 4637-4652;

    9. [9]

      (b) K.A. Henzler-Wildman, V. Thai, M. Lei, et al., Intrinsic motions along an enzymatic reaction trajectory, Nature 450 (2007) 838-844.

    10. [10]

      [6] W. Pendergast, B.R. Yerxa, J.G. Douglass, et al., Synthesis and P2Y receptor activity of a series of uridine dinucleoside 5'-polyphosphates, Bioorg. Med. Chem. Lett. 11 (2001) 157-160.

    11. [11]

      [7] L.C. Davies, J.A. Stock, S.E. Barrie, et al., Dinucleotide analogues as inhibitors of thymidine kinase, thymidylate kinase, and ribonucleotide reductase, J. Med. Chem. 31 (1988) 1305-1308.

    12. [12]

      [8] (a) P. Feldhau, T. Fröhlich, R.S. Goody, et al., Synthetic inhibitors of adenylate kinases in the assays for ATPases and phosphokinases, Eur. J. Biochem. 57 (1975) 197-204;

    13. [13]

      (b) J. Köhrle, K.S. Boos, E. Schlimme, Preparation of [14C]-P1,P5-di(adenosine 50- )pentaphosphate by direct reaction of [14C]-adenosine 50-diphosphate with activated adenosine 50-triphosphate, Liebigs Ann. Chem. (1977) 1160-1166;

    14. [14]

      (c) A. Hampton, F. Kappler, D. Picker, Species- or isozyme-specific enzyme inhibitors. 4. Design of a two-site inhibitor of adenylate kinase with isozyme selectivity, J. Med. Chem. 25 (1982) 638-644.

    15. [15]

      [9] Q. Han, B.L. Gaffney, R.A. Jones, One-flask synthesis of dinucleoside tetra- and pentaphosphates, Org. Lett. 8 (2006) 2075-2077.

    16. [16]

      [10] S. Mohamady, S.D. Taylor, Synthesis of nucleoside tetraphosphates and dinucleoside pentaphosphates via activation of cyclic trimetaphosphate, Org. Lett. 15 (2013) 2612-2615.

    17. [17]

      [11] (a) Q. Sun, S.S. Gong, J. Sun, et al., A P(V)-N activation strategy for synthesis of nucleoside polyphosphates, J. Org. Chem. 78 (2013) 8417-8426;

    18. [18]

      (b) Q. Sun, S.S. Gong, J. Sun, et al., Efficient synthesis of nucleoside 5'-triphosphates and their β,γ-bridging oxygen-modified analogs from nucleoside 5'-phosphates, Tetrahedron Lett. 55 (2014) 2114-2118;

    19. [19]

      (c) Q. Sun, J. Sun, S.S. Gong, et al., Efficient synthesis of 5-hydroxymethyl-, 5- formyl-, and 5-carboxyl-2'-deoxycytidine and their triphosphates, RSC Adv. 4 (2014) 36036-36039;

    20. [20]

      (d) Q. Sun, S.S. Gong, S. Liu, et al., 4,5-Dicyanoimidazole-promoted synthesis of dinucleoside polyphosphates and their analogs, Tetrahedron 70 (2014) 4500-4506;

    21. [21]

      (e) Q. Sun, X.J. Li, J. Sun, et al., An improved P(V)-N activation strategy for the synthesis of nucleoside diphosphate 6-deoxy-L-sugars, Tetrahedron 70 (2014) 294-300;

    22. [22]

      (f) Q. Sun, S. Liu, J. Sun, et al., An H-phosphonate strategy for the synthesis of 2', 3'-dideoxynucleoside triphosphates and homodinucleotides, Chin. Chem. Lett. 25 (2014) 427-430.

    23. [23]

      [12] (a) A.R. Kore, Z. Xiao, A. Senthilvelan, et al., An efficient synthesis of pyrimidine specific 2'-deoxynucleoside-5'-tetraphosphates, Nucleosides Nucleotides Nucleic Acids 31 (2012) 567-573;

    24. [24]

      (b) A.R. Kore, A. Senthilvelan, M. Shanmugasundaram, A new, facile, and protection- free one-pot chemical synthesis of 2'-deoxynucleoside-5'-tetraphosphates, Tetrahedron Lett. 53 (2012) 5868-5870.

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