Abstract
A gas chromatographic method using electron capture detection for determination of the stereochemical composition of chiralolatile compounds, e.g., pheromones, at the picogram level is described. Substances of interest are analyzed as pentafluorobenzoate derivatives on fused silica capillary columns coated with CP Sil-88. This method was developed primarily for the quantitative analyses of stereoisomerism of the pheromone precursor, diprionol, in female sawflies,Neodiprion sertifer. It was possible to separate the stereoisomers showing (2S, 3S, 7R) and (2S, 3S, 7S) configurations. Resolution of the (2S, 3S, 7S)- and (2S, 3R, 7R)-diastereomers was high enough to allow the quantification of these stereoisomers. A quantitative analysis of the diprionol production in individualN. sertifer females yielded 7.5–9.7 ng/female.
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Bergström, G., Wassgren, A.-B., Högberg, H.-E., Hedenström, E., Hefetz, A., Simon, D., Ohlsson, T., andLöfqvist, J. 1992. Species-species, two-component, volatile signals in two sympatric ant-lion species:Synclysis baetica andAcanthaclisis occitanica (Neuroptera, Myrmeleontidae).J. Chem. Ecol. 18:1177–1188.
Fogelqvist, E., Josefsson, B., andRoos, C. 1980. Determination of carboxylic acids and phenols in water by extractive alkylation using pentafluorobenzylation, glass capillary GC and electron capture detection.HRC CC 3:568–574.
Högberg, H.-E., Hedenström, E., Wassgren, A.-B., Hjalmarsson, M., Bergström, G., Löfqvist, J., andNorin, T. 1990. Synthesis and gas chromatographic separation of the eight stereoisomers of diprionol and their acetates, components of the sex pheromone of pine sawflies.Tetrahedron 46:3007–3018.
Kawahara, F.K. 1968. Microdetermination of derivatives of phenols and mercaptans by means of electron capture gas chromatography.Anal. Chem. 40:1009–1010.
Kern, H., andBrander, B. 1979. Precision of an automated all-glass capillary gas chromatography system with an electron capture detector for the trace analysis of estrogens.HRC CC 2:312–318.
König, W.A. 1982. Separation of enantiomers by capillary gas chromatography with chiral stationary phases.HRC CC 5:588–595.
König, W.A., Francke, W., andBenecke, I. 1982. Gas chromatographic enantiomer separation of chiral alcohols.J. Chromatogr. 239:227–231.
König, W.A., Krebber, R., Evers, P., andBruhn, G. 1990. Stereochemical analysis of constituents of essential oils and flavor compounds by enantioselective capillary gas chromatography.HRC CC 13:328–332.
Sattar, M.A., andPaasivirta, J. 1979. Simultaneous determination of 4-chloro-2-methylphen-oxyacetic acid and its metabolites in soil by gas chromatography.Anal. Chem. 51:598–602.
Schurig, V., andWeber, R. 1984. Use of glass and fused-silica open tubular columns for the separation of structural, configurational and optical isomers by selective complexation gas chromatography.J. Chromatogr. 289:321–332.
Ställberg-Stenhagen, S. 1970. The absolute configuration of terrestrol.Acta Chem. Scand. 24:358–360.
Wassgren, A.-B., andBergström, G. 1984. A simple effluent splitter for capillary gas chromatography.HRC CC 7:154–155.
Wassgren, A.-B., Anderbrant, O., Löfqvist, J., Hansson, B., Bergström, G., Hedenström, E., andHögberg, H.-E. 1992. Pheromone related compounds in pupal and adult female pine sawflies,Neodiprion sertifer, of different age and in different parts of the body.J. Insect Physiol. 38:885–893.
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Wassgren, AB., Bergström, G. Quantitative high-resolution gas chromatographic determination of stereoisomeric composition of chiral volatile compounds in the picogram range by ec-detection. J Chem Ecol 21, 987–994 (1995). https://doi.org/10.1007/BF02033803
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DOI: https://doi.org/10.1007/BF02033803