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J Org Chem

Title:		Synthesis and use of stereospecifically deuterated analogues of palmitic Acid to investigate the stereochemical course of the delta11 desaturase of the processionary moth
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. jlaqob@iiqab.csis.es"
Journal Title:		J Org Chem
Year:		2004
Volume:		69
Issue:		21
Page Number:		7108 - 7113
DOI:		10.1021/jo049320h
ISSN/ISBN:		0022-3263 (Print) 0022-3263 (Linking)
Abstract:		"Thaumetopoea 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 Delta(11) 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 Delta(11) 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"
Keywords:		Animals Deuterium/chemistry Fatty Acid Desaturases/*chemistry Molecular Structure Moths/*chemistry Palmitic Acids/*chemical synthesis/*chemistry Sex Attractants/chemical synthesis/chemistry Species Specificity Stereoisomerism;
Notes:		"MedlineAbad, Jose-Luis Villorbina, Gemma Fabrias, Gemma Camps, Francisco eng Research Support, Non-U.S. Gov't 2004/10/09 J Org Chem. 2004 Oct 15; 69(21):7108-13. doi: 10.1021/jo049320h"