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Synthesis and use of stereospecifically deuterated analogues of palmitic Acid to investigate the stereochemical course of the Δ11 desaturase of the processionary moth

AutorAbad, José Luis; Villorbina, Gemma; Fabriàs, Gemma; Camps Díez, Francisco
Palabras claveThaumetopoea pityocampa
Sex pheromones
Palmitic acids
T. pityocampa
Δ11 Desaturase
Fecha de publicación14-sep-2004
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 69(21): 7108-7113 (2004)
ResumenThaumetopoea pityocampa pheromone glands contain desaturases that, after several sequential reactions from palmitic acid, catalyze the formation of a unique enyne fatty acid, which is the immediate sex pheromone precursor. In this article, we describe the synthesis of different stereospecifically deuterium-labeled and isotopically tagged palmitic acid probes needed to decipher the stereochemical course of the T. pityocampa Δ11 desaturase. The synthesis of probes has been carried out by a chemoenzymatic route, in which the key step is the kinetic lipase-catalyzed resolution of racemic mixtures of secondary propargyl alcohols. The presence of the acetylenic bond simplifies the absolute configuration determination of the resolved alcohols. Moreover, it allows the introduction of the isotopic tag by deuteration. By use of the probes thus prepared, experimental evidence is presented that the Δ11 desaturase of T. pityocampa transforms palmitic acid into (Z)-11-hexadecenoic acid by removal of the pro-(R)-hydrogen atoms from both C11 and C12.
Descripción6 pages, 3 figures, 2 schemes.-- PMID: 15471459 [PubMed].-- Printed version published Oct 15, 2004.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo049320h
Versión del editorhttp://dx.doi.org/10.1021/jo049320h
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