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Chiral discrimination using piezoelectric and optical gas sensors

Nature volume 387, pages 577–580 (1997)Cite this article

Abstract

Odour perception in humans can sometimes discriminate different enantiomers of a chiral compound1,2,3, such as limonene. Chiral discrimination represents one of the greatest challenges in attempts to devise selective and sensitive gas sensors. The importance of such discrimination for pharmacology is clear, as the physiological effect of enantiomers of drugs and other biologically active molecules may differ significantly4. Here we describe two different sensor systems that are capable of recognizing different enantiomers and of qualitatively monitoring the enantiomeric composition of amino-acid derivatives and lactates in the gas phase. One sensor detects changes in mass, owing to binding of the compound being analysed (the ‘analyte’), by thickness shear-mode resonance5,6,7; the other detects changes in the thickness of a surface layer by reflectometric interference spectroscopy8,9,10. Both devices use the two enantiomers of a chiral polymeric receptor, and offer rapid on-line detection of chiral species with high selectivity.

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Figure 1: The principle of chiral recognition by gas sensors: chiral discrimination by preferential sorption of the enantiomers of N-trifluoroacetyl-alanin methyl ester (N-TFA-Ala-OMe) into enantioselective (R)- and (S)-octyl-Chirasil-Val polymers.
Figure 2: Signal transduction techniques.
Figure 3: Normalized (with regard to the frequency shift due to polymer deposition) TSMR responses to different concentrations (p/p0 adjusted pressure with respect to the saturation vapour pressure at 298K) of (R)-, (S)- and racemic N-trifluoroacetyl-alanin methyl ester.
Figure 4: Top, relative RIFS-sensor signals (normalized with regard to the layer thickness without analyte gas, as described in the text of two chiral sensors ((S)-sensor, solid line; (R)-sensor, dotted line) and an additional SE-30-sensor (dashed line) upon exposure to different enantiomeric compositions of methyl lactate.

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Acknowledgements

We thank H.-G. Brendle, R. Schlunk and B. Christian at the Institute of Organic Chemistry of the University of Tübingen for providing the enantioselective polymers and the chiral analyte N-TFA-Ala-OMe. This work was supported by the Deutsche Forschungsgemeinschaft.

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Authors and Affiliations

  1. Institute of Physical and Theoretical Chemistry, Centre of Interface Analysis and Sensors, Auf der Morgenstelle 8, D-72076, Tbingen, Germany

    K. Bodenhöfer, J. Seemann, G. Gauglitz & W. Gpel

  2. *,

    A. Hierlemann

  3. †Institute of Organic Chemistry, University of Tbingen, Auf der Morgenstelle 8, D-72076, Tbingen, Germany

    B. Koppenhoefer

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  1. K. Bodenhöfer
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Correspondence to W. Gpel.

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Bodenhöfer, K., Hierlemann, A., Seemann, J. et al. Chiral discrimination using piezoelectric and optical gas sensors. Nature 387, 577–580 (1997). https://doi.org/10.1038/42426

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