Regio- and stereospecific syntheses and nitric oxide donor properties of (E)-9- and (E)-10-nitrooctadec-9-enoic acids
Regio- and stereospecific syntheses and nitric oxide donor properties of (E)-9- and (E)-10-nitrooctadec-9-enoic acids
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DOI：
10.1021/ol060548w
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发表时间：
2006-05-25
期刊：
影响因子：
5.2
通讯作者：
King, S. Bruce
中科院分区：
文献类型：
--
作者：
Gorczynski, Michael J.;Huang, Jinming;King, S. Bruce
硝化脂肪酸作为内源性过氧化物酶体增殖体激活受体γ (PPAR γ)配体和一氧化氮（NO）供体。本文首次以顺式环烯酸和单甲基壬二酸为原料，合成了(E)-9-硝基十八烯-9-烯酸(1)和(E)-10-硝基十八烯-9-烯酸(2)这两种区域异构体硝基油酸。这些合成依赖于九碳硝基组分和九碳醛之间的亨利缩合。初步的化学发光NO检测研究揭示了这些硝化脂肪酸释放NO的能力。
Nitrated fatty acids act as endogenous peroxisome proliferator-activated receptor gamma(PPAR gamma) ligands and nitric oxide (NO) donors. We describe the first specific preparation of the two regioisomers of nitrooleic acid, (E)-9-nitrooctadec-9-enoic acid (1) and (E)-10-nitrooctadec-9-enoic acid (2), from cis-cyclooctene and monomethyl azelate, respectively. These syntheses rely upon a Henry condensation between a nine-carbon nitro component and a nine-carbon aldehyde. Preliminary chemiluminescence NO detection studies reveal the ability of these nitrated fatty acids to release NO.