Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A new approach to the synthesis of polyunsaturated deuterated isoprostanes: total synthesis of d4-5-epi-8,12-iso-iPF3alpha-VI and d4-8,12-iso-iPF3alpha-VI.

Literature DB >> 19846297

A new approach to the synthesis of polyunsaturated deuterated isoprostanes: total synthesis of d4-5-epi-8,12-iso-iPF3alpha-VI and d4-8,12-iso-iPF3alpha-VI.

Chih-Tsung Chang¹, Pranav Patel, Vivek Gore, Wen-Liang Song, John A Lawson, William S Powell, Garret A Fitzgerald, Joshua Rokach.

Abstract

The total and stereospecific synthesis of d(4)-5-epi-8,12-iso-iPF(3alpha)-VI 55 and d(4)-8,12-iso-iPF(3alpha)-VI 64, EPA-derived all-syn-isoprostanes (iPs), has been accomplished. Because of issues related to volatility and yield with some of the primary deuterated synthons an improved synthesis is presented. These two deuterated analogs were used to discover and quantify the presence of the corresponding endogenous isoprostanes in human urine. These assays may serve as a valuable index of oxidative stress in population with omega-3 fatty acid enriched diets containing eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and may also be useful as an index of the severity of inflammatory diseases such as atherosclerosis and Alzheimer's disease.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2009 PMID： 19846297 PMCID： PMC2783685 DOI： 10.1016/j.bmcl.2009.09.099

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

17 in total

Review 1. Isoprostanes: formation, analysis and use as indices of lipid peroxidation in vivo.

Authors: J A Lawson; J Rokach; G A FitzGerald
Journal: J Biol Chem Date: 1999-08-27 Impact factor: 5.157

2. Biomarkers of oxidative stress study II: are oxidation products of lipids, proteins, and DNA markers of CCl4 poisoning?

Authors: M B Kadiiska; B C Gladen; D D Baird; D Germolec; L B Graham; C E Parker; A Nyska; J T Wachsman; B N Ames; S Basu; N Brot; G A Fitzgerald; R A Floyd; M George; J W Heinecke; G E Hatch; K Hensley; J A Lawson; L J Marnett; J D Morrow; D M Murray; J Plastaras; L J Roberts; J Rokach; M K Shigenaga; R S Sohal; J Sun; R R Tice; D H Van Thiel; D Wellner; P B Walter; K B Tomer; R P Mason; J C Barrett
Journal: Free Radic Biol Med Date: 2005-03-15 Impact factor: 7.376

3. Reductive Deprotection of Silyl Groups with Wilkinson's Catalyst/Catechol Borane.

Authors: Pranav Patel; Chih-Tsung Chang; Namin Kang; Gue-Jae Lee; William S Powell; Joshua Rokach
Journal: Tetrahedron Lett Date: 2007-07-23 Impact factor: 2.415

4. Eicosapentaenoic-acid-derived isoprostanes: synthesis and discovery of two major isoprostanes.

Authors: Chih-Tsung Chang; Pranav Patel; Namin Kang; John A Lawson; Wen-Liang Song; William S Powell; Garret A FitzGerald; Joshua Rokach
Journal: Bioorg Med Chem Lett Date: 2008-09-06 Impact factor: 2.823

5. Synthesis of the eight enantiomerically pure diastereomers of the 12-F(2)-isoprostanes.

Authors: Douglass F Taber; Ming Xu; John C Hartnett
Journal: J Am Chem Soc Date: 2002-11-06 Impact factor: 15.419

6. Preparation of isoprostanes and neuroprostanes.

Authors: Long Guo Quan; Jin Kun Cha
Journal: J Am Chem Soc Date: 2002-10-23 Impact factor: 15.419

7. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism.

Authors: J D Morrow; K E Hill; R F Burk; T M Nammour; K F Badr; L J Roberts
Journal: Proc Natl Acad Sci U S A Date: 1990-12 Impact factor: 11.205

A new approach to the synthesis of polyunsaturated deuterated isoprostanes: total synthesis of d4-5-epi-8,12-iso-iPF3alpha-VI and d4-8,12-iso-iPF3alpha-VI.

Review 1. Isoprostanes: formation, analysis and use as indices of lipid peroxidation in vivo.

2. Biomarkers of oxidative stress study II: are oxidation products of lipids, proteins, and DNA markers of CCl4 poisoning?

3. Reductive Deprotection of Silyl Groups with Wilkinson's Catalyst/Catechol Borane.

4. Eicosapentaenoic-acid-derived isoprostanes: synthesis and discovery of two major isoprostanes.

5. Synthesis of the eight enantiomerically pure diastereomers of the 12-F(2)-isoprostanes.

6. Preparation of isoprostanes and neuroprostanes.

7. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism.

8. Diastereoselective Synthesis of an Isoprostane: (+/-)-8-epi-PGF(2)(alpha) Ethyl Ester.

Review 9. Lipid peroxidation in aging brain and Alzheimer's disease.

10. Novel eicosapentaenoic acid-derived F3-isoprostanes as biomarkers of lipid peroxidation.

1. Bioactive products formed in humans from fish oils.