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Substrate-Dependent Stereochemical Course of the (Z)-13-Desaturation Catalyzed by the Processionary Moth Multifunctional Desaturase.

AutorAbad, José Luis; Camps Díez, Francisco; Fabriàs, Gemma
Palabras claveSubstrate
Dependent Stereochemical Course of the (Z)-13-Desaturation
Catalyzed by the Processionary Moth Multifunctional Desaturase
Fecha de publicación11-sep-2007
EditorAmerican Chemical Society
CitaciónJournal of the American Chemical Society; vol 129, 15007-15012
ResumenThe stereochemical course of the ¢13 desaturation involved in the biosynthesis of Thaumetopoea pityocampa sex pheromone was studied using stereotopically labeled and tagged palmitic acids as metabolic probes. In the synthetic pathway, a functionalized acetylene common synthon was used for introducing the four deuterium tags. Further coupling of the tetradeuterated synthon to the appropriated alkynol and a double chemoenzymatic strategy to resolve the alcohol functionality allowed one to obtain the enantiomerically enriched probes used in the mechanistic studies. Mass spectrometric analyses of extracts from tissues cultured with each probe revealed that removal of the C13 and C14 hydrogens in 11-hexadecynoate and (Z)-11-hexadecenoate are pro-(R)- and pro-(S)-specific syn-dehydrogenation processes, respectively. This finding constitutes the first example in the literature of an enzymatic (Z)-desaturation exhibiting a substrate-dependent stereochemical course.
Descripción6 páginas, 6 figuras, 3 esquemas, 1 tabla.
Versión del editorhttp://dx.doi.org/10.1021/ja0751936
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