Literature DB >> 16119935

Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC.

Michael E Jung1, Judith A Berliner, Daniela Angst, Dawei Yue, Lukasz Koroniak, Andrew D Watson, Rongsong Li.   

Abstract

A total synthesis of the naturally occurring hydroxy ketone PEIPC 1, a compound that plays a role in endothelial activation in atherosclerosis, has been completed via a triply convergent preparation of a protected EI derivative 13 from 3,5-diacetoxycyclopentene 7, pentane-1,5-diol, and vinyllithium, using Sharpless epoxidation and enzymatic resolution as key steps. Final coupling with lyso-PC 16 and silyl group deprotection gave PECPC 2 and PEIPC 1, which showed the same activity as natural PECPC and PEIPC. [reaction: see text]

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Year:  2005        PMID： 16119935     DOI： 10.1021/ol051415y

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


  10 in total

1.  An epoxyisoprostane is a major regulator of endothelial cell function.

Authors:  Wei Zhong; James R Springstead; Ramea Al-Mubarak; Sangderk Lee; Rongsong Li; Benjamin Emert; Judith A Berliner; Michael E Jung
Journal:  J Med Chem       Date:  2013-10-31       Impact factor: 7.446

Review 2.  Role of phospholipid oxidation products in atherosclerosis.

Authors:  Sangderk Lee; Konstantin G Birukov; Casey E Romanoski; James R Springstead; Aldons J Lusis; Judith A Berliner
Journal:  Circ Res       Date:  2012-08-31       Impact factor: 17.367

3.  Fatty acid epoxyisoprostane E2 stimulates an oxidative stress response in endothelial cells.

Authors:  Xinmin Yan; Sangderk Lee; B Gabriel Gugiu; Lukasz Koroniak; Michael E Jung; Judith Berliner; Jinluo Cheng; Rongsong Li
Journal:  Biochem Biophys Res Commun       Date:  2014-01-14       Impact factor: 3.575

Review 4.  Structural identification and cardiovascular activities of oxidized phospholipids.

Authors:  Robert G Salomon
Journal:  Circ Res       Date:  2012-09-14       Impact factor: 17.367

5.  Host-derived oxidized phospholipids and HDL regulate innate immunity in human leprosy.

Authors:  Daniel Cruz; Andrew D Watson; Christopher S Miller; Dennis Montoya; Maria-Teresa Ochoa; Peter A Sieling; Miguel A Gutierrez; Mohamad Navab; Srinivasa T Reddy; Joseph L Witztum; Alan M Fogelman; Thomas H Rea; David Eisenberg; Judith Berliner; Robert L Modlin
Journal:  J Clin Invest       Date:  2008-08       Impact factor: 14.808

6.  Ox-PAPC activation of PMET system increases expression of heme oxygenase-1 in human aortic endothelial cell.

Authors:  Sangderk Lee; Rongsong Li; Brandon Kim; Roland Palvolgyi; Tiffany Ho; Qian-Zhou Yang; Jason Xu; Wan Lam Szeto; Henry Honda; Judith A Berliner
Journal:  J Lipid Res       Date:  2008-08-29       Impact factor: 5.922

7.  Improved synthesis of the epoxy isoprostane phospholipid PEIPC and its reactivity with amines.

Authors:  Michael E Jung; Judith A Berliner; Lukasz Koroniak; B Gabriel Gugiu; Andrew D Watson
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005

Review 8.  Lipid peroxidation generates biologically active phospholipids including oxidatively N-modified phospholipids.

Authors:  Sean S Davies; Lilu Guo
Journal:  Chem Phys Lipids       Date:  2014-04-02       Impact factor: 3.329

9.  A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.

Authors:  Aleksandr Grisin; P Andrew Evans
Journal:  Chem Sci       Date:  2015-08-06       Impact factor: 9.825

10.  Concise enantiospecific total synthesis of tubingensin A.

Authors:  Adam E Goetz; Amanda L Silberstein; Michael A Corsello; Neil K Garg
Journal:  J Am Chem Soc       Date:  2014-02-18       Impact factor: 15.419
  10 in total

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