« Previous AbstractPopulation-specific responses of floral volatiles to abiotic factors in changing environments    Next Abstract"Quantitative metabolome, proteome and transcriptome analysis of midgut and fat body tissues in the mountain pine beetle, Dendroctonus ponderosae Hopkins, and insights into pheromone biosynthesis" »

J Chem Ecol

Title:		Preparative chiral liquid chromatography for enantiomeric separation of pheromones
Author(s):		Keeling CI; Ngo HT; Benusic KD; Slessor KN;
Address:		"Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada"
Journal Title:		J Chem Ecol
Year:		2001
Volume:		27
Issue:		3
Page Number:		487 - 497
DOI:		10.1023/a:1010380704106
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"Cellulose triacetate was investigated as a chiral stationary phase for preparatively separating the enantiomers of lineatin, frontalin, exo-brevicomin, endo-brevicomin, verbenone, (E)-conophthorin, and grandisol. Tens of milligrams of both enantiomers were efficiently prepared in high percentage enantiomeric excess from one injection of each compound except grandisol. We prepared grandisyl acetate, benzoate, and 4-bromobenzoate to determine if derivatization of the free alcohol might improve separation. Of these, grandisyl 4-bromobenzoate provided the best separation but was still not very well resolved. Preparative separation of enantiomers on cellulose triacetate is a viable alternative to stereoselective synthesis when semiochemicals of very high enantiomeric purity are required for biological testing"
Keywords:		"Bicyclic Monoterpenes Bridged Bicyclo Compounds, Heterocyclic/chemistry/isolation & purification Cellulose/*analogs & derivatives/*chemistry Chromatography, Liquid/*methods Pheromones/chemistry/*isolation & purification *Pyrans Stereoisomerism Terpenes/ch;"
Notes:		"MedlineKeeling, C I Ngo, H T Benusic, K D Slessor, K N eng Research Support, Non-U.S. Gov't 2001/07/10 J Chem Ecol. 2001 Mar; 27(3):487-97. doi: 10.1023/a:1010380704106"