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Literature DB >> 18754590

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

Michael E Jung¹, Judith A Berliner, Lukasz Koroniak, B Gabriel Gugiu, Andrew D Watson.

Abstract

An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E 2- sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2008 PMID： 18754590 PMCID： PMC2712226 DOI： 10.1021/ol8014804

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

8 in total

1. Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC.

Authors: Michael E Jung; Judith A Berliner; Daniela Angst; Dawei Yue; Lukasz Koroniak; Andrew D Watson; Rongsong Li
Journal: Org Lett Date: 2005-09-01 Impact factor: 6.005

2. Total synthesis of 2-(5,6-epoxyisoprostane A2)phosphorylcholine and elucidation of the relative configuration of the isoprostane moiety.

Authors: Hukum P Acharya; Yuichi Kobayashi
Journal: Angew Chem Int Ed Engl Date: 2005-05-30 Impact factor: 15.336

3. Epoxyisoprostane and epoxycyclopentenone phospholipids regulate monocyte chemotactic protein-1 and interleukin-8 synthesis. Formation of these oxidized phospholipids in response to interleukin-1beta.

Authors: Ganesamoorthy Subbanagounder; Jason W Wong; Hans Lee; Kym F Faull; Elizabeth Miller; Joseph L Witztum; Judith A Berliner
Journal: J Biol Chem Date: 2001-12-19 Impact factor: 5.157

4. Structural identification of a novel pro-inflammatory epoxyisoprostane phospholipid in mildly oxidized low density lipoprotein.

Authors: A D Watson; G Subbanagounder; D S Welsbie; K F Faull; M Navab; M E Jung; A M Fogelman; J A Berliner
Journal: J Biol Chem Date: 1999-08-27 Impact factor: 5.157

5. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo.

Authors: A D Watson; N Leitinger; M Navab; K F Faull; S Hörkkö; J L Witztum; W Palinski; D Schwenke; R G Salomon; W Sha; G Subbanagounder; A M Fogelman; J A Berliner
Journal: J Biol Chem Date: 1997-05-23 Impact factor: 5.157

6. Oxidatively truncated docosahexaenoate phospholipids: total synthesis, generation, and Peptide adduction chemistry.

Authors: Xiaorong Gu; Mingjiang Sun; Bogdan Gugiu; Stanley Hazen; John W Crabb; Robert G Salomon
Journal: J Org Chem Date: 2003-05-16 Impact factor: 4.354

7. Protein targets of oxidized phospholipids in endothelial cells.

Authors: B Gabriel Gugiu; Kevin Mouillesseaux; Victoria Duong; Tabitha Herzog; Avetis Hekimian; Lukasz Koroniak; Thomas M Vondriska; Andrew D Watson
Journal: J Lipid Res Date: 2007-12-10 Impact factor: 5.922

8. Oxidized phospholipid-induced endothelial cell/monocyte interaction is mediated by a cAMP-dependent R-Ras/PI3-kinase pathway.

Authors: Amy L Cole; Ganesamoorthy Subbanagounder; Srirupa Mukhopadhyay; Judith A Berliner; Devendra K Vora
Journal: Arterioscler Thromb Vasc Biol Date: 2003-06-12 Impact factor: 8.311

8 in total

10 in total

1. Network for activation of human endothelial cells by oxidized phospholipids: a critical role of heme oxygenase 1.

Authors: Casey E Romanoski; Nam Che; Fen Yin; Nguyen Mai; Delila Pouldar; Mete Civelek; Calvin Pan; Sangderk Lee; Ladan Vakili; Wen-Pin Yang; Paul Kayne; Imran N Mungrue; Jesus A Araujo; Judith A Berliner; Aldons J Lusis
Journal: Circ Res Date: 2011-07-07 Impact factor: 17.367

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

1. Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC.

2. Total synthesis of 2-(5,6-epoxyisoprostane A2)phosphorylcholine and elucidation of the relative configuration of the isoprostane moiety.

3. Epoxyisoprostane and epoxycyclopentenone phospholipids regulate monocyte chemotactic protein-1 and interleukin-8 synthesis. Formation of these oxidized phospholipids in response to interleukin-1beta.

4. Structural identification of a novel pro-inflammatory epoxyisoprostane phospholipid in mildly oxidized low density lipoprotein.

5. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo.

6. Oxidatively truncated docosahexaenoate phospholipids: total synthesis, generation, and Peptide adduction chemistry.

7. Protein targets of oxidized phospholipids in endothelial cells.

8. Oxidized phospholipid-induced endothelial cell/monocyte interaction is mediated by a cAMP-dependent R-Ras/PI3-kinase pathway.

1. Network for activation of human endothelial cells by oxidized phospholipids: a critical role of heme oxygenase 1.

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

Review 3. Role of phospholipid oxidation products in atherosclerosis.

4. Evidence for the importance of OxPAPC interaction with cysteines in regulating endothelial cell function.

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

Review 6. Structural identification and cardiovascular activities of oxidized phospholipids.

7. Fragmented oxidation products define barrier disruptive endothelial cell response to OxPAPC.

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

9. Synthesis of Bioconjugate Sesterterpenoids with Phospholipids and Polyunsaturated Fatty Acids.

10. Concise enantiospecific total synthesis of tubingensin A.