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dc.contributor.authorAbad, José Luis-
dc.contributor.authorVillorbina, Gemma-
dc.contributor.authorFabriàs, Gemma-
dc.contributor.authorCamps Díez, Francisco-
dc.identifier.citationLipids 38(8): 865-871 (2003)en_US
dc.description7 pages, 1 figure, 1 scheme.-- PMID: 14577666 [PubMed].-- Available online Nov 17, 2006.en_US
dc.description.abstractTo study the activity of the different desaturases present in the pheromone biosynthetic pathway of the Egyptian armyworm, Spodoptera littoralis, we prepared a series of mono-and gem-difluorinated analogs of myristic acid with halogen substitution at the C8–C11 positions of the aliphatic chain via specifically positioned dithiane precursors. Thus, transformation of dithianes by treatment with N-bromosuccinimide in the presence of H2O followed by reduction with LiAIH4 afforded the appropriate alcohols, which reacted with diethylaminosulfur trifluoride to give rise to the corresponding monofluoroderivative intermediates. Alternatively, the introduction of the gem-difluoro functionality was carried out by reaction of the appropriate dithiane intermediate with 1,3-dibromo-5,5-dimethylhydantoin in the presence of HF/pyridine. The activity of these fluorinated FA as substrates and inhibitors of the desaturases involved in the biosynthesis of the sex pheromonal blend of S. littoralis has been studied. In this case, 11-fluorotetradecanoic acid elicited a moderate inhibitory activity of Δ11 desaturase.en_US
dc.description.sponsorshipFinancial support for this work by the Comisión Interministerial de Ciencia y Tecnología and the Fondo Europeo de Desarrollo Regional (grant AGL-2001-0585), Comissionat per a Universitats i Recerca from the Generalitat de Catalunya (grant 2001SGR-00342) and Sociedad Española de Desarrollos Químicos.en_US
dc.format.extent22195 bytes-
dc.subjectEgyptian armywormen_US
dc.subjectSpodoptera littorialisen_US
dc.subjectPheromone biosynthetic pathwayen_US
dc.subjectSex pheromone biosynthesisen_US
dc.subjectEnzyme inhibitionen_US
dc.titleSynthesis of fluorinated analogs of myristic acid as potential inhibitors of egyptian armyworm (Spodoptera littorialis) Δ11 desaturasedesaturaseen_US
dc.description.peerreviewedPeer revieweden_US
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