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.
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.
Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, Melbourne, FL 32901, USA.
Chih-Tsung
CT
Chang
Pranav
P
Patel
Vivek
V
Gore
Wen-Liang
WL
Song
John A
JA
Lawson
William S
WS
Powell
Garret A
GA
Fitzgerald
Joshua
J
Rokach
D015118:Eicosapentaenoic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000652:urine; D006801:Humans; D028421:Isoprostanes / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000652:urine; D015394:Molecular Structure; D013237:Stereoisomerism
C515332:8,12-iso-iPF3alpha-VI; D028421:Isoprostanes; D015118:Eicosapentaenoic Acid