Literature DB >> 16774263

Synthesis and molecular recognition of phosphatidylinositol-3-methylenephosphate.

Joanna Gajewiak1, Yong Xu, Stephanie A Lee, Tatiana G Kutateladze, Glenn D Prestwich.   

Abstract

[reaction: see text] Phosphatidylinositol-3-phosphate (PtdIns(3)P) is a spatial regulator of vesicular trafficking and other vital cellular processes. We describe the asymmetric total synthesis of a metabolically stabilized analogue, phosphatidylinositol-3-methylenephosphate (PtdIns(3)MP) from a differentially protected myo-inositol. NMR studies of PtdIns(3)MP bound to the (15)N-labeled FYVE domain showed significant (1)H and (15)N chemical shift changes relative to the unliganded protein.

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Year:  2006        PMID： 16774263      PMCID： PMC2535797          DOI： 10.1021/ol060903i

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  20 in total

Review 1.  Class I phosphoinositide 3-kinases.

Authors:  Karen E Anderson; Shaun P Jackson
Journal:  Int J Biochem Cell Biol       Date:  2003-07       Impact factor: 5.085

2.  Chemical synthesis and molecular recognition of phosphatase-resistant analogues of phosphatidylinositol-3-phosphate.

Authors:  Yong Xu; Stephanie A Lee; Tatiana G Kutateladze; Diego Sbrissa; Assia Shisheva; Glenn D Prestwich
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

3.  FYVE fingers bind PtdIns(3)P.

Authors:  J M Gaullier; A Simonsen; A D'Arrigo; B Bremnes; H Stenmark; R Aasland
Journal:  Nature       Date:  1998-07-30       Impact factor: 49.962

4.  Phosphatidylinositol 3-phosphate recognition by the FYVE domain.

Authors:  T G Kutateladze; K D Ogburn; W T Watson; T de Beer; S D Emr; C G Burd; M Overduin
Journal:  Mol Cell       Date:  1999-06       Impact factor: 17.970

Review 5.  Acyclic nucleoside phosphonates: a key class of antiviral drugs.

Authors:  Erik De Clercq; Antonín Holý
Journal:  Nat Rev Drug Discov       Date:  2005-11       Impact factor: 84.694

Review 6.  Phosphoinositide signaling; from affinity probes to pharmaceutical targets.

Authors:  Glenn D Prestwich
Journal:  Chem Biol       Date:  2004-05

7.  Phosphonomethylphosphorylmethyl(oxy)-analogues of geranylgeranyl diphosphate as stable and selective geranylgeranyl protein transferase inhibitors.

Authors:  Filippo Minutolo; Michela Antonello; Silvia Barontini; Simone Bertini; Laura Betti; Romano Danesi; Gianbattista Gervasi; Gino Giannaccini; Chiara Papi; Giorgio Placanica; Simona Rapposelli; Marco Macchia
Journal:  Farmaco       Date:  2004-11

8.  Targeting of the FYVE domain to endosomal membranes is regulated by a histidine switch.

Authors:  Stephanie A Lee; Rosemary Eyeson; Matthew L Cheever; Jinming Geng; Vladislav V Verkhusha; Christopher Burd; Michael Overduin; Tatiana G Kutateladze
Journal:  Proc Natl Acad Sci U S A       Date:  2005-09-02       Impact factor: 11.205

Review 9.  Myotubularins, a large disease-associated family of cooperating catalytically active and inactive phosphoinositides phosphatases.

Authors:  Jocelyn Laporte; Florence Bedez; Alessandra Bolino; Jean-Louis Mandel
Journal:  Hum Mol Genet       Date:  2003-08-12       Impact factor: 6.150

10.  PI3P signaling regulates receptor sorting but not transport in the endosomal pathway.

Authors:  A Petiot; J Faure; H Stenmark; J Gruenberg
Journal:  J Cell Biol       Date:  2003-09-15       Impact factor: 10.539
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  4 in total

1.  Synthesis and biological activity of PTEN-resistant analogues of phosphatidylinositol 3,4,5-trisphosphate.

Authors:  Honglu Zhang; Nicolas Markadieu; Renaud Beauwens; Christophe Erneux; Glenn D Prestwich
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

2.  Metabolically stabilized derivatives of phosphatidylinositol 4-phosphate: synthesis and applications.

Authors:  Ju He; Joanna Gajewiak; Jordan L Scott; Denghuang Gong; Muzaffar Ali; Michael D Best; Glenn D Prestwich; Robert V Stahelin; Tatiana G Kutateladze
Journal:  Chem Biol       Date:  2011-10-28

Review 3.  Phosphatase-resistant analogues of lysophosphatidic acid: agonists promote healing, antagonists and autotaxin inhibitors treat cancer.

Authors:  Glenn D Prestwich; Joanna Gajewiak; Honglu Zhang; Xiaoyu Xu; Guanghui Yang; Monica Serban
Journal:  Biochim Biophys Acta       Date:  2008-04-08

4.  Stabilized phosphatidylinositol-5-phosphate analogues as ligands for the nuclear protein ING2: chemistry, biology, and molecular modeling.

Authors:  Wei Huang; Honglu Zhang; Foteini Davrazou; Tatiana G Kutateladze; Xiaobing Shi; Or Gozani; Glenn D Prestwich
Journal:  J Am Chem Soc       Date:  2007-05-01       Impact factor: 15.419
  4 in total

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