English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/20465
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:

Title

Synthesis of fluorinated analogs of myristic acid as potential inhibitors of egyptian armyworm (Spodoptera littorialis) Δ11 desaturasedesaturase

AuthorsAbad, José Luis ; Villorbina, Gemma; Fabriàs, Gemma ; Camps Díez, Francisco
KeywordsEgyptian armyworm
Spodoptera littorialis
Pheromone biosynthetic pathway
Sex pheromone biosynthesis
Enzyme inhibition
Issue DateAug-2003
PublisherSpringer
CitationLipids 38(8): 865-871 (2003)
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.
Description7 pages, 1 figure, 1 scheme.-- PMID: 14577666 [PubMed].-- Available online Nov 17, 2006.
Publisher version (URL)http://dx.doi.org/10.1007/s11745-003-1137-2
URIhttp://hdl.handle.net/10261/20465
DOI10.1007/s11745-003-1137-2
ISSN0024-4201
E-ISSN1558-9307
Appears in Collections:(IQAC) Artículos
Files in This Item:
File Description SizeFormat 
Abad_Jose_Luis_et_al.pdf271,72 kBAdobe PDFThumbnail
View/Open
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.