Literature DB >> 19606206

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

Katherine J Kayser-Bricker1, Peter A Jordan, Scott J Miller.   

Abstract

Peptide-based catalysts have been applied to the enantioselective syntheses of the title compounds, with this being the first report of the synthesis of an ent-PI5P analogue. The key steps in the synthesis involve asymmetric phosphorylation catalysis. Additional maneuvers were developed with a protecting groups scheme that enabled efficient, streamlined syntheses of these important mediators of biochemical events.

Entities:  

Year:  2008        PMID： 19606206      PMCID： PMC2673006          DOI： 10.1016/j.tet.2008.03.037

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  20 in total

1.  NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities.

Authors:  Hugo E. Gottlieb; Vadim Kotlyar; Abraham Nudelman
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

2.  Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic: a concise total synthesis of D-myo-inositol-1-phosphate.

Authors:  B R Sculimbrene; S J Miller
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

3.  Preparation of L-alpha-phosphatidyl-D-myo-inositol 3-phosphate (3-PIP) and 3,5-bisphosphate (3,5-PIP2).

Authors:  J R Falck; U M Krishna; J H Capdevila
Journal:  Bioorg Med Chem Lett       Date:  2000-08-07       Impact factor: 2.823

4.  Unified total syntheses of the inositol polyphosphates: D-I-3,5,6P3, D-I-3,4,5P3, D-I-3,4,6P3, and D-I-3,4,5,6P4 via catalytic enantioselective and site-selective phosphorylation.

Authors:  Adam J Morgan; Shio Komiya; Yingju Xu; Scott J Miller
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

5.  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

6.  Inositol lipids are regulated during cell cycle progression in the nuclei of murine erythroleukaemia cells.

Authors:  J H Clarke; A J Letcher; C S D'santos; J R Halstead; R F Irvine; N Divecha
Journal:  Biochem J       Date:  2001-08-01       Impact factor: 3.857

7.  PtdIns5P activates the host cell PI3-kinase/Akt pathway during Shigella flexneri infection.

Authors:  Caroline Pendaries; Hélène Tronchère; Laurence Arbibe; Joelle Mounier; Or Gozani; Lewis Cantley; Michael J Fry; Frédérique Gaits-Iacovoni; Philippe J Sansonetti; Bernard Payrastre
Journal:  EMBO J       Date:  2006-02-16       Impact factor: 11.598

8.  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

9.  The only inositol tetrakisphosphate detectable in avian erythrocytes is the isomer lacking phosphate at position 3: a NMR study.

Authors:  G W Mayr; W Dietrich
Journal:  FEBS Lett       Date:  1987-03-23       Impact factor: 4.124

10.  Identification of a new polyphosphoinositide in plants, phosphatidylinositol 5-monophosphate (PtdIns5P), and its accumulation upon osmotic stress.

Authors:  H J Meijer; C P Berrie; C Iurisci; N Divecha; A Musgrave; T Munnik
Journal:  Biochem J       Date:  2001-12-01       Impact factor: 3.857
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  3 in total

1.  Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate.

Authors:  Peter A Jordan; Katherine J Kayser-Bricker; Scott J Miller
Journal:  Proc Natl Acad Sci U S A       Date:  2010-05-03       Impact factor: 11.205

Review 2.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

3.  A fully synthetic and biochemically validated phosphatidyl inositol-3-phosphate hapten via asymmetric synthesis and native chemical ligation.

Authors:  Brent D Chandler; Anne L Burkhardt; Klaudia Foley; Courtney Cullis; Denise Driscoll; Natalie Roy D'Amore; Scott J Miller
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419
  3 in total

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