用于研究斜纹夜蛾中(11E)-去饱和反应的示踪剂[14,14,14-2H₃]12-羟基十四烷酸和[13,14-2H₂]11-羟基十四烷酸的合成。
Synthesis of [14,14,14-2H3] 12-hydroxytetradecanoic acid and [13,14-2H2] 11-hydroxytetradecanoic acid useful as tracers to study a (11E)-desaturation reaction in Spodoptera littoralis.
作者信息
Navarro I, Fabriás G, Camps F
机构信息
Department of Biological Organic Chemistry, CID-CSIC, Barcelona, Spain.
出版信息
Bioorg Med Chem. 1996 Mar;4(3):439-43. doi: 10.1016/0968-0896(96)00023-5.
The synthesis of deuterium labeled 11- and 12-hydroxytetradecanoic acids to study a (11E) desaturase in the moth Spodoptera littoralis is reported. [14,14,14-2H3] 12-hydroxytetradecanoic acid was synthesized in four steps from 11-iodo-1-undecene in 49% overall yield. Deuterium was introduced by reaction of an epoxy ester with (CD3)2CuLi. The preparation of [13,14-2H2] 11-hydroxytetradecanoic acid was carried out in six steps from 11-bromoundecanoic acid in 55% overall yield. In this case, label was introduced by deuteration of an homoallyl alcohol with D2, using the Wilkinson catalyst. Incubation of pheromone glands with either of both acids did not lead to the formation of the labeled (11E)-tetradecenoic acid.
报道了氘标记的11-和12-羟基十四烷酸的合成，用于研究棉铃虫中的一种（11E）去饱和酶。[14,14,14-2H3]12-羟基十四烷酸由11-碘-1-十一碳烯经四步合成，总产率为49%。通过环氧酯与(CD3)2CuLi反应引入氘。[13,14-2H2]11-羟基十四烷酸由11-溴代十一烷酸经六步合成，总产率为55%。在这种情况下，使用威尔金森催化剂通过用D2对高烯丙醇进行氘代引入标记。用这两种酸中的任何一种孵育性信息素腺都不会导致标记的（11E）-十四碳烯酸的形成。
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