Metabolically stabilized derivatives of phosphatidylinositol 4-phosphate: Synthesis and applications

Chemistry and Biology

Volumn 18, Issue 10, 2011, Pages 1312-1319

  He, Ju ^a   Gajewiak, Joanna ^b   Scott, Jordan L ^c   Gong, Denghuang ^d   Ali, Muzaffar ^a   Best, Michael D ^d   Prestwich, Glenn D ^b   Stahelin, Robert V ^c,e   Kutateladze, Tatiana G ^a  

^a UNIVERSITY OF COLORADO SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF NOTRE DAME   (United States)

^d UNIVERSITY OF TENNESSEE   (United States)

^e INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 PALMITOYL 2 OLEOYLPHOSPHATIDYLETHANOLAMINE; 1-PALMITOYL-2-OLEOYLPHOSPHATIDYLCHOLINE; 1-PALMITOYL-2-OLEOYLPHOSPHATIDYLETHANOLAMINE; 2 OLEOYL 1 PALMITOYLPHOSPHATIDYLCHOLINE; HYBRID PROTEIN; INOSITOL 1,4 BIS(PHOSPHATE); INOSITOL 1,4-BIS(PHOSPHATE); INOSITOL PHOSPHATE; LIGAND; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHATIDYLINOSITOL; PHOSPHATIDYLINOSITOL 4 PHOSPHATE; PHOSPHATIDYLINOSITOL 4-PHOSPHATE; PLEKHA3 PROTEIN, HUMAN; POLYPHOSPHOINOSITIDE; SIGNAL TRANSDUCING ADAPTOR PROTEIN;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; LIPID BILAYER; METABOLISM; MOLECULAR PROBE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; PROTEIN TERTIARY STRUCTURE; SIGNAL TRANSDUCTION; SYNTHESIS;

ADAPTOR PROTEINS, SIGNAL TRANSDUCING; BINDING SITES; INOSITOL PHOSPHATES; LIGANDS; LIPID BILAYERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR PROBES; MOLECULAR STRUCTURE; PHOSPHATIDYLCHOLINES; PHOSPHATIDYLETHANOLAMINES; PHOSPHATIDYLINOSITOL PHOSPHATES; PHOSPHATIDYLINOSITOLS; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY; RECOMBINANT FUSION PROTEINS; SIGNAL TRANSDUCTION;

EUKARYOTA;

EID: 80055100618     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2011.07.022     Document Type: Article

References (22)

1. G. D'Angelo, M. Vicinanza, A. Di Campli, and M.A. De Matteis The multiple roles of PtdIns(4)P - not just the precursor of PtdIns(4,5)P2 J. Cell Sci. 121 2008 1955 1963 (Pubitemid 352015192)
2. F. Delaglio, S. Grzesiek, G.W. Vuister, G. Zhu, J. Pfeifer, and A. Bax NMRPipe: a multidimensional spectral processing system based on UNIX pipes J. Biomol. NMR 6 1995 277 293
3. S. Dowler, R.A. Currie, D.G. Campbell, M. Deak, G. Kular, C.P. Downes, and D.R. Alessi Identification of pleckstrin-homology-domain-containing proteins with novel phosphoinositide-binding specificities Biochem. J. 351 2000 19 31
4. K.M. Ferguson, J.M. Kavran, V.G. Sankaran, E. Fournier, S.J. Isakoff, E.Y. Skolnik, and M.A. Lemmon Structural basis for discrimination of 3-phosphoinositides by pleckstrin homology domains Mol. Cell 6 2000 373 384
5. J. Gajewiak, Y. Xu, S.A. Lee, T.G. Kutateladze, and G.D. Prestwich Synthesis and molecular recognition of phosphatidylinositol-3-methylenephosphate Org. Lett. 8 2006 2811 2813
6. A. Godi, A. Di Campli, A. Konstantakopoulos, G. Di Tullio, D.R. Alessi, G.S. Kular, T. Daniele, P. Marra, J.M. Lucocq, and M.A. De Matteis FAPPs control Golgi-to-cell-surface membrane traffic by binding to ARF and PtdIns(4)P Nat. Cell Biol. 6 2004 393 404 (Pubitemid 38607499)
7. D. Gong, H.E. Bostic, M.D. Smith, and M.D. Best Synthesis of modular headgroup conjugates corresponding to all seven phosphatidylinositol polyphosphate isomers for convenient probe generation European J. Org. Chem. 2009 4170 4179
8. C.J. Hamilton, and S.M. Roberts Synthesis of fluorinated phosphonoacetate derivatives of carbocyclic nucleoside monophosphonates and activity as inhibitors of HIV reverse transcriptase J. Chem. Soc., Perkin Trans. 1 1999 1051 1056
9. J. He, R.M. Haney, M. Vora, V.V. Verkhusha, R.V. Stahelin, and T.G. Kutateladze Molecular mechanism of membrane targeting by the GRP1 PH domain J. Lipid Res. 49 2008 1807 1815
10. J. He, J.L. Scott, A. Heroux, S. Roy, M. Lenoir, M. Overduin, R.V. Stahelin, and T.G. Kutateladze Molecular basis of phosphatidylinositol 4-phosphate and ARF1 recognition by the FAPP1 PH domain J. Biol. Chem. 286 2011 18650 18657
11. J. He, M. Vora, R.M. Haney, G.S. Filonov, C.A. Musselman, C.G. Burd, A.G. Kutateladze, V.V. Verkhusha, R.V. Stahelin, and T.G. Kutateladze Membrane insertion of the FYVE domain is modulated by pH Proteins 76 2009 852 860
12. R.A. Hom, M. Vora, M. Regner, O.M. Subach, W. Cho, V.V. Verkhusha, R.V. Stahelin, and T.G. Kutateladze pH-dependent binding of the Epsin ENTH domain and the AP180 ANTH domain to PI(4,5)P2-containing bilayers J. Mol. Biol. 373 2007 412 423 (Pubitemid 47445580)
13. W. Huang, H. Zhang, F. Davrazou, T.G. Kutateladze, X. Shi, O. Gozani, and G.D. Prestwich Stabilized phosphatidylinositol-5-phosphate analogues as ligands for the nuclear protein ING2: chemistry, biology, and molecular modeling J. Am. Chem. Soc. 129 2007 6498 6506
14. R.J. Kubiak, and K.S. Bruzik Comprehensive and uniform synthesis of all naturally occurring phosphorylated phosphatidylinositols J. Org. Chem. 68 2003 960 968 (Pubitemid 36176620)
15. S.A. Lee, J. Kovacs, R.V. Stahelin, M.L. Cheever, M. Overduin, T.G. Setty, C.G. Burd, W. Cho, and T.G. Kutateladze Molecular mechanism of membrane docking by the Vam7p PX domain J. Biol. Chem. 281 2006 37091 37101 (Pubitemid 46042179)
16. M.A. Lemmon Membrane recognition by phospholipid-binding domains Nat. Rev. Mol. Cell Biol. 9 2008 99 111 (Pubitemid 351158910)
17. M. Lenoir, U. Coskun, M. Grzybek, X. Cao, S.B. Buschhorn, J. James, K. Simons, and M. Overduin Structural basis of wedging the Golgi membrane by FAPP pleckstrin homology domains EMBO Rep. 11 2010 279 284
18. S.E. Lietzke, S. Bose, T. Cronin, J. Klarlund, A. Chawla, M.P. Czech, and D.G. Lambright Structural basis of 3-phosphoinositide recognition by pleckstrin homology domains Mol. Cell 6 2000 385 394
19. T.F.J. Martin Phosphoinositide lipids as signaling molecules: common themes for signal transduction, cytoskeletal regulation, and membrane trafficking Annu. Rev. Cell Dev. Biol. 14 1998 231 264 (Pubitemid 29001455)
20. F. Minutolo, M. Antonello, S. Barontini, S. Bertini, L. Betti, R. Danesi, G. Gervasi, G. Giannaccini, C. Papi, and G. Placanica Phosphonomethylphosphorylmethyl(oxy)-analogues of geranylgeranyl diphosphate as stable and selective geranylgeranyl protein transferase inhibitors Farmaco 59 2004 887 892 (Pubitemid 39488369)
21. D.P. Phillion, and S.S. Andrew Synthesis and reactivity of diethyl phosphonomethyltriflate Tetrahedron Lett. 27 1986 1477 1480
22. W.F. Vranken, W. Boucher, T.J. Stevens, R.H. Fogh, A. Pajon, M. Llinas, E.L. Ulrich, J.L. Markley, J. Ionides, and E.D. Laue The CCPN data model for NMR spectroscopy: development of a software pipeline Proteins 59 2005 687 696 (Pubitemid 40695845)