Literature DB >> 12558421

Comprehensive and uniform synthesis of all naturally occurring phosphorylated phosphatidylinositols.

Robert J Kubiak1, Karol S Bruzik.   

Abstract

Studies of cellular signal transduction mechanisms involving receptor-mediated generation of inositol phosphates and phosphorylated phosphatidylinositols require easy access to these naturally occurring products. Although numerous synthetic methods have been developed during the past decade, most of these methods suffer from excessive length and lack of generality. In this work we describe the comprehensive and uniform synthesis of all naturally occurring phosphatidylinositols such as phosphatidylinositol, phosphatidylinositol 3-phosphate, 4-phosphate, 5-phosphate, 3,4-bisphosphate, 3,5-bisphosphate, 4,5-bisphosphate, and 3,4,5-trisphosphate, featuring both saturated and unsaturated fatty acid chains.

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Year:  2003        PMID: 12558421     DOI: 10.1021/jo0206418

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  19 in total

1.  Synthesis and biological activity of phospholipase C-resistant analogues of phosphatidylinositol 4,5-bisphosphate.

Authors:  Honglu Zhang; Yong Xu; Zheng Zhang; Emily R Liman; Glenn D Prestwich
Journal:  J Am Chem Soc       Date:  2006-05-03       Impact factor: 15.419

Review 2.  The "Other" Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo-Inositol Chemistry).

Authors:  Mark P Thomas; Stephen J Mills; Barry V L Potter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

3.  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

4.  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

5.  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

6.  Synthesis and molecular recognition of phosphatidylinositol-3-methylenephosphate.

Authors:  Joanna Gajewiak; Yong Xu; Stephanie A Lee; Tatiana G Kutateladze; Glenn D Prestwich
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

7.  Fluorescent phosphatidylinositol 4,5-bisphosphate derivatives with modified 6-hydroxy group as novel substrates for phospholipase C.

Authors:  Xiaoyang Wang; Matthew Barrett; John Sondek; T Kendall Harden; Qisheng Zhang
Journal:  Biochemistry       Date:  2012-06-22       Impact factor: 3.162

8.  Catalyst-Dependent Syntheses of Phosphatidylinositol-5 Phosphate-DiC8 and its Enantiomer.

Authors:  Katherine J Kayser-Bricker; Peter A Jordan; Scott J Miller
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

9.  5-Stabilized phosphatidylinositol 3,4,5-trisphosphate analogues bind Grp1 PH, inhibit phosphoinositide phosphatases, and block neutrophil migration.

Authors:  Honglu Zhang; Ju He; Tatiana G Kutateladze; Takahiro Sakai; Takehiko Sasaki; Nicolas Markadieu; Christophe Erneux; Glenn D Prestwich
Journal:  Chembiochem       Date:  2010-02-15       Impact factor: 3.164

10.  Microplate-based characterization of protein-phosphoinositide binding interactions using a synthetic biotinylated headgroup analogue.

Authors:  Denghuang Gong; Matthew D Smith; Debasis Manna; Heidi E Bostic; Wonhwa Cho; Michael D Best
Journal:  Bioconjug Chem       Date:  2009-02       Impact factor: 4.774

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