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Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy

Author

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  • Angelika Kühnle

    (Interdisciplinary Nanoscience Center at University of Aarhus (iNANO) and Institute of Physics and Astronomy, University of Aarhus)

  • Trolle R. Linderoth

    (Interdisciplinary Nanoscience Center at University of Aarhus (iNANO) and Institute of Physics and Astronomy, University of Aarhus)

  • Bjørk Hammer

    (Interdisciplinary Nanoscience Center at University of Aarhus (iNANO) and Institute of Physics and Astronomy, University of Aarhus)

  • Flemming Besenbacher

    (Interdisciplinary Nanoscience Center at University of Aarhus (iNANO) and Institute of Physics and Astronomy, University of Aarhus)

Abstract

Stereochemistry plays a central role in controlling molecular recognition and interaction: the chemical and biological properties of molecules depend not only on the nature of their constituent atoms but also on how these atoms are positioned in space. Chiral specificity is consequently fundamental in chemical biology and pharmacology1,2 and has accordingly been widely studied. Advances in scanning probe microscopies now make it possible to probe chiral phenomena at surfaces at the molecular level. These methods have been used to determine the chirality of adsorbed molecules3,4,5, and to provide direct evidence for chiral discrimination in molecular interactions6 and the spontaneous resolution of adsorbates into extended enantiomerically pure overlayers3,7,8,9. Here we report scanning tunnelling microscopy studies of cysteine adsorbed to a (110) gold surface, which show that molecular pairs formed from a racemic mixture of this naturally occurring amino acid are exclusively homochiral, and that their binding to the gold surface is associated with local surface restructuring. Density-functional theory10 calculations indicate that the chiral specificity of the dimer formation process is driven by the optimization of three bonds on each cysteine molecule. These findings thus provide a clear molecular-level illustration of the well known three-point contact model11,12 for chiral recognition in a simple bimolecular system.

Suggested Citation

  • Angelika Kühnle & Trolle R. Linderoth & Bjørk Hammer & Flemming Besenbacher, 2002. "Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy," Nature, Nature, vol. 415(6874), pages 891-893, February.
  • Handle: RePEc:nat:nature:v:415:y:2002:i:6874:d:10.1038_415891a
    DOI: 10.1038/415891a
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    Cited by:

    1. Zhen-Yu Yi & Xue-Qing Yang & Jun-Jie Duan & Xiong Zhou & Ting Chen & Dong Wang & Li-Jun Wan, 2022. "Evolution of Br⋯Br contacts in enantioselective molecular recognition during chiral 2D crystallization," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Yunjun Cao & Joel Mieres-Perez & Julien Frederic Rowen & Elsa Sanchez-Garcia & Wolfram Sander & Karina Morgenstern, 2023. "Chirality control of a single carbene molecule by tip-induced van der Waals interactions," Nature Communications, Nature, vol. 14(1), pages 1-7, December.

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