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Lipids

Title:		Synthesis of fluorinated analogs of myristic acid as potential inhibitors of Egyptian armyworm (Spodoptera littoralis) delta11 desaturase
Author(s):		Abad JL; Villorbina G; Fabrias G; Camps F;
Address:		"Departamento de Quimica Organica Biologica, Instituto de Investigaciones Quimicas y Ambientales de Barcelona, Consejo Superior de Investigaciones Cientificas, 08034, Barcelona, Spain"
Journal Title:		Lipids
Year:		2003
Volume:		38
Issue:		8
Page Number:		865 - 871
DOI:		10.1007/s11745-003-1137-2
ISSN/ISBN:		0024-4201 (Print) 0024-4201 (Linking)
Abstract:		"To 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 LiAlH4 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 delta11 desaturase"
Keywords:		"Animals Egypt Enzyme Inhibitors/chemical synthesis/chemistry/pharmacology Fatty Acid Desaturases/*antagonists & inhibitors/metabolism Fluorine/*chemistry Models, Molecular Molecular Structure Myristic Acid/*chemical synthesis/chemistry/*pharmacology Spodo;"
Notes:		"MedlineAbad, Jose-Luis Villorbina, Gemma Fabrias, Gemma Camps, Francisco eng Research Support, Non-U.S. Gov't 2003/10/28 Lipids. 2003 Aug; 38(8):865-71. doi: 10.1007/s11745-003-1137-2"