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dc.contributor.authorAbad, José Luis-
dc.contributor.authorRodríguez Ropero, Sergio-
dc.contributor.authorCamps Díez, Francisco-
dc.contributor.authorFabriàs, Gemma-
dc.identifier.citationThe Jornal of Organic Chemistry 71(20): 7558-7564 (2006)en_US
dc.description7 pages, 1 table, 4 figures, 2 schemes.en_US
dc.description.abstractThaumetopoea pityocampa pheromone glands contain an unusual Δ11 acetylenase that produces an alkynoic fatty acid intermediate in the sex pheromone biosynthetic pathway of this species. In this article, we describe the synthesis and use of the deuterated (Z)-11-hexadecenoic acid probes required to decipher the cryptoregiochemistry of this enzyme. The label in the olefinic bonds was introduced by Wittig reaction between the appropriate deuterated reagents. Besides the vinyl deuterium atoms, for reliable GC−MS analyses these compounds bear a tetradeuterium tag, which was introduced by deuteration of an alkyne intermediate in the presence of the Wilkinson catalyst. Pheromone gland metabolization studies of these probes provided experimental evidence that the transformation of (Z)-11-hexadecenoic acid into 11-hexadecynoic acid by the Δ11 acetylenase takes place by a stepwise mechanism, in which a significant perturbation of the strong vinyl C11−H bond occurs prior to a fast elimination of the vinyl hydrogen at C-12.en_US
dc.description.sponsorshipWe gratefully acknowledge CICYT and FEDER (AGL2001-0585) and Generalitat de Catalunya (2001SGR 00342) for financial support. J.-L.A. thanks Spanish MEC for a Ramón y Cajal contract. The authors also acknowledge Rodolfo Hernández from Laboratorio de Sanidad Forestal (Gobierno de Aragón, Mora de Rubielos, Teruel) for providing T. pityocampa female pupae.en_US
dc.format.extent19968 bytes-
dc.publisherAmerican Chemical Societyen_US
dc.subjectThaumetopoea pityocampa pheromone glandsen_US
dc.subjectAlkynoic fatty aciden_US
dc.subjectZ-11-hexadecenoic aciden_US
dc.subject11-hexadecynoic aciden_US
dc.subjectVinyl hydrogen at C-12en_US
dc.titleSynthesis and Use of Probes to Investigate the Cryptoregiochemistry of the First Animal Acetylenaseen_US
dc.description.peerreviewedPeer revieweden_US
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