Synlett 2014; 25(11): 1494-1498
DOI: 10.1055/s-0033-1341079
synpacts
© Georg Thieme Verlag Stuttgart · New York

Diphosphoinositol Polyphosphates: Polar Stars in Cell Signaling

Henning Jacob Jessen*
University of Zürich, Department of Chemistry, Winterthurerstrasse 190, 8057 Zürich, Switzerland   Fax: +41(44)6356812   eMail: Henningjacob.jessen@chem.uzh.ch
,
Samanta Capolicchio
University of Zürich, Department of Chemistry, Winterthurerstrasse 190, 8057 Zürich, Switzerland   Fax: +41(44)6356812   eMail: Henningjacob.jessen@chem.uzh.ch
,
Igor Pavlovic
University of Zürich, Department of Chemistry, Winterthurerstrasse 190, 8057 Zürich, Switzerland   Fax: +41(44)6356812   eMail: Henningjacob.jessen@chem.uzh.ch
,
Divyeshsinh Takhtasinh Thakor
University of Zürich, Department of Chemistry, Winterthurerstrasse 190, 8057 Zürich, Switzerland   Fax: +41(44)6356812   eMail: Henningjacob.jessen@chem.uzh.ch
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 28. Januar 2014

Accepted after revision: 06. März 2014

Publikationsdatum:
03. April 2014 (online)


Abstract

The propagation of information inside cells is achieved in nature by small diffusible molecules. Many of these secondary messengers are highly charged species derived from myo-inositol. The diphosphoinositol polyphosphates (X-PP-myo-InsP5) represent a novel group of secondary messengers that regulate various important biological processes. Depending on the phosphorylation pattern, these molecules can occur in symmetric or nonsymmetric forms. In a recent study, we have shown the potential of C2 symmetric phosphoramidites as reagents for desymmetrizing myo-inositol and for obtaining all four possible nonsymmetric X-PP-myo-InsP5 stereoisomers in enantiomerically pure form. These results and their potential implications for the design of tools for chemical biology are discussed.

 
  • References

  • 1 Best MD, Zhang HL, Prestwich GD. Nat. Prod. Rep. 2010; 27: 1403
  • 2 Lemmon MA. Nat. Rev. Mol. Cell. Biol. 2008; 9: 99
    • 3a Menniti FS, Miller RN, Putney JW. Jr, Shears SB. J. Biol. Chem. 1993; 268: 3850
    • 3b Stephens L, Radenberg T, Thiel U, Vogel G, Khoo KH, Dell A, Jackson TR, Hawkins PT, Mayr GW. J. Biol. Chem. 1993; 268: 4009
  • 4 Saiardi A, Bhandari R, Resnick AC, Snowman AM, Snyder SH. Science 2004; 306: 2101
  • 5 Hand CE, Honek JF. Bioorg. Med. Chem. Lett. 2007; 17: 183
    • 6a Bhandari R, Saiardi A, Ahmadibeni Y, Snowman AM, Resnick AC, Kristiansen TZ, Molina H, Pandey A, Werner JK. Jr, Juluri KR, Xu Y, Prestwich GD, Parang K, Snyder SH. Proc. Natl. Acad. Sci. U.S.A. 2007; 104: 15305
    • 6b For a related recent study on peptide pyrophosphorylation, see: Marmelstein AM, Yates LM, Conway JH, Fiedler D. J. Am. Chem. Soc. 2014; 136: 108
    • 7a Chakraborty A, Koldobskiy MA, Bello NT, Maxwell M, Potter JJ, Juluri KR, Maag D, Kim S, Huang AS, Dailey MJ, Saleh M, Snowman AM, Moran TH, Mezey E, Snyder SH. Cell 2010; 143: 897
    • 7b Pulloor NK, Nair S, Kostic AD, Bist P, Weaver JD, Riley AM, Tyagi R, Uchil PD, York JD, Snyder SH, García-Sastre A, Potter BV. L, Lin R, Shears SB, Xavier RJ, Krishnan MN. PLoS Pathog. 2014; 10: e1003981
    • 8a Shears SB, Weaver JD, Wang H. Adv. Biol. Regul. 2013; 53: 19
    • 8b Wilson MS, Livermore TM, Saiardi A. Biochem. J. 2013; 452: 369
    • 8c Thomas MP, Potter BV. FEBS J. 2014; 281: 14
  • 9 Luo HR, Huang YE, Chen JC, Saiardi A, Iijima M, Ye K, Huang Y, Nagata E, Devreotes P, Snyder SH. Cell 2003; 114: 559
    • 10a Shears SB. Mol. Pharmacol. 2009; 76: 236
    • 10b Kilari RS, Weaver JD, Shears SB, Safrany ST. FEBS Lett. 2013; 587: 3464
    • 10c Wundenberg T, Mayr GW. Biol. Chem. 2012; 393: 979
  • 11 Gokhale NA, Zaremba A, Janoshazi AK, Weaver JD, Shears SB. Biochem. J. 2013; 453: 413
  • 12 Lin H, Fridy PC, Ribeiro AA, Choi JH, Barma DK, Vogel G, Falck JR, Shears SB, York JD, Mayr GW. J. Biol. Chem. 2009; 284: 1863
  • 13 Loss O, Azevedo C, Szijgyarto Z, Bosch D, Saiardi A. J. Vis. Exp. 2011; (55) e3027; doi:10.3791/3027
    • 14a Reddy KM, Reddy KK, Falck JR. Tetrahedron Lett. 1997; 38: 4951
    • 14b Zhang H, Thompson J, Prestwich GD. Org. Lett. 2009; 11: 1551
    • 14c Wu M, Dul BE, Trevisan AJ, Fiedler D. Chem. Sci. 2013; 4: 405
    • 14d Falck JR, Reddy KK, Ye JH, Saady M, Mioskowski C, Shears SB, Tan Z, Safrany S. J. Am. Chem. Soc. 1995; 117: 12172
    • 14e Albert C, Safrany ST, Bembenek ME, Reddy KM, Reddy K, Falck J, Brocker M, Shears SB, Mayr GW. Biochem. J. 1997; 327: 553
  • 15 Capolicchio S, Thakor DT, Linden A, Jessen HJ. Angew. Chem. Int. Ed. 2013; 52: 6912
    • 16a Sculimbrene BR, Xu Y, Miller SJ. J. Am. Chem. Soc. 2004; 126: 13182
    • 16b Jordan PA, Kayser-Bricker KJ, Miller SJ. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20620
  • 17 Cremosnik GS, Hofer A, Jessen HJ. Angew. Chem. Int. Ed. 2014; 53: 286
  • 18 Riley AM, Wang HC, Weaver JD, Shears SB, Potter BV. L. Chem. Commun. 2012; 48: 11292
  • 19 Jessen HJ, Schulz T, Balzarini J, Meier C. Angew. Chem. Int. Ed. 2008; 47: 8719
    • 20a Wang H, Falck JR, Hall TM. T, Shears SB. Nat. Chem. Biol. 2012; 8: 111
    • 20b Pisani F, Livermore T, Rose G, Chubb JR, Gaspari M, Saiardi A. PLoS One 2014; 9: e85533
    • 21a Azevedo C, Burton A, Ruiz-Mateos E, Marsh M, Saiardi A. Proc. Natl. Acad. Sci. U.S.A. 2009; 106: 21161
    • 21b Shears S. Proc. Natl. Acad. Sci. U. S. A. 2010; 107: E17; author reply: E18
  • 22 Subramanian D, Laketa V, Müller R, Tischer C, Zarbakhsh S, Pepperkok R, Schultz C. Nat. Chem. Biol. 2010; 6: 324
  • 23 Allen JJ, Lazerwith SE, Shokat KM. J. Am. Chem. Soc. 2005; 127: 5288