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.
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.
复制标题
多不饱和氘代异前列烷合成新方法：d4-5-epi-8,12-iso-iPF3alpha-VI和d4-8,12-iso-iPF3alpha-VI的全合成。
DOI：
10.1016/j.bmcl.2009.09.099
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发表时间：
2009
影响因子：
2.7
通讯作者：
Rokach,Joshua
中科院分区：
文献类型：
--
作者：
Chang,Chih-Tsung;Patel,Pranav;Gore,Vivek;Song,Wen-Liang;Lawson,JohnA;Powell,WilliamS;Fitzgerald,GarretA;Rokach,Joshua
完成了全同位异前列烷(IPs)的全合成和立体专一性合成，分别为d4-5-epi-8，12-iso-iPF3α-VI 55和d4-8，12-iso-iPF3α-VI。由于与挥发性和产率有关的问题，一些初级的氚合成子，提出了一种改进的合成。这两个氢化类似物被用来发现和定量人类尿液中相应的内源性异前列烷的存在。这些分析可以作为富含omega-3脂肪酸的饮食中含有二十碳五烯酸(EPA)和二十二碳六烯酸(DHA)的人群氧化应激的有价值的指标，也可以作为动脉粥样硬化和阿尔茨海默病等炎症性疾病的严重程度的指标。
The total and stereospecific synthesis of d4-5-epi-8,12-iso-iPF3α-VI 55 and d4-8,12-iso-iPF3α-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.