Abstract
Chirality is a fundamental aspect of chemical biology, and is of central importance in pharmacology. Consequently there is great interest in techniques for distinguishing between different chiral forms of a compound. Chemical force microscopy is a technique that combines chemical discrimination with atomic force microscopy by chemical derivatization of the scanning probe tip. It has been applied to the study of hydrophobic and hydrophilic interactions1, the binding between biotin and streptavidin2,3 and between DNA bases4. Here we report on the use of chemical force microscopy to discriminate between chiral molecules. Using chiral molecules attached to the probe tip, we can distinguish the two enantiomers of mandelic acid arrayed on a surface, through differences in both the adhesion forces and the frictional forces measured by the probe.
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References
Frisbie, C. D., Rozsnyai, L. F., Noy, A., Wrighton, M. S. & Lieber, C. M. Functional group imaging by chemical force microscopy. Science 265, 2071–2074 (1994).
Lee, G. U., Kidwell, D. A. & Colton, R. J. Sensing discrete streptavidin–biotin interactions with atomic force microscopy. Langmuir 10, 354–357 (1994).
Ludwig, M., Dettmann, W. & Gaub, H. E. Atomic force microscope imaging contrast based on molecular recognition. Biophys. J. 72, 445–448 (1997).
Boland, T. & Ratner, B. D. Direct measurement of hydrogen bonding in DNA nucleotide bases by atomic force microscopy. Proc. Natl Acad. Sci. USA 92, 5297–5301 (1995).
Israelachvili, J. Intermolecular and Surface Forces(Academic, New York, 1992).
Pirkle, W. H., Finn, J. M., Schreiner, J. L. & Hamper, B. C. Awidely useful chiral stationary phase for the high-performance liquid chromatography separation of enantiomers. J. Am. Chem. Soc. 103, 3964–3966 (1981).
Weis, R. M. & McConnell, H. M. Two-dimensional chiral crystals of phospholipid. Nature 310, 47–49 (1984).
Stevens, F., Dyer, D. J. & Walba, D. M. Direct observation of enantiomorphous monolayer crystals from enantiomers by scanning tunneling microscopy. Angew. Chem. Int. Edn Engl. 35, 900–901 (1996).
Johnson, K. L. Continuum mechanics of adhesion and friction. Langmuir 12, 4510–4513 (1996).
Noy, A., Frisbie, C. D., Rozsnyai, L. F., Wrighton, M. S., Lieber, C. M. Chemical Force Microscopy: exploiting chemically-modified tips to quantify adhesion, friction and functional group distribution in molecular assemblies. J. Am. Chem. Soc. 117, 7943–7951 (1995).
Yoshizawa, H., Chen, Y.-L. & Israelachvili, J. Fundamental mechanism of interfacial friction. I. Relation between adhesion and friction. J. Phys. Chem. 97, 4128–4140 (1993).
Lantz, A. M., O'Shea, S. J., Welland, M. E. & Johnson, K. L. Atomic force microscope study of contact area and friction on NbSe2. Phys. Rev. B 55, 10776–10785 (1997).
Sader, J. E., Larson, I., Mulvaney, P. & White, L. R. Method for the calibration of atomic force microscope cantilevers. Rev. Sci. Instrum. 66, 3789–3798 (1995).
Kumar, A. & Whitesides, G. M. Features of gold having micrometer to centimeter dimensions can be formed with an elastomeric stamp and an alkanethiol “ink” followed by chemical etching. Appl. Phys. Lett. 63, 2002–2004 (1993).
Acknowledgements
We thank S. O'Shea for discussions, G. Whitesides (Harvard University) and H.Bieybuck (IBM Zurich) for providing microcontact stamps, and R. Mellor for programming. We acknowledge financial support from Zeneca for a studentship (R.A.M.), and EPSRC for a postdoctoral fellowship (M.-E.T.).
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McKendry, R., Theoclitou, ME., Rayment, T. et al. Chiral discrimination by chemical force microscopy. Nature 391, 566–568 (1998). https://doi.org/10.1038/35339
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DOI: https://doi.org/10.1038/35339
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