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

AuthorsAbad, José Luis CSIC ORCID ; Camps Díez, Francisco; Fabriàs, Gemma CSIC ORCID
Dependent Stereochemical Course of the (Z)-13-Desaturation
Catalyzed by the Processionary Moth Multifunctional Desaturase
Issue Date11-Sep-2007
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society; vol 129, 15007-15012
AbstractThe 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.
Description6 páginas, 6 figuras, 3 esquemas, 1 tabla.
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