Visualizing Chiral Interactions in Carbohydrates Adsorbed on Au(111) by High‐Resolution STM Imaging

Research output: Contribution to journalArticleResearchpeer review

Authors

  • Johannes Seibel
  • Giulio Fittolani
  • Hossein Mirhosseini
  • Xu Wu
  • Stephan Rauschenbach
  • Kelvin Anggara
  • Peter H. Seeberger
  • Martina Delbianco
  • Thomas D. Kühne
  • Uta Schlickum
  • Klaus Kern
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Details

Original languageEnglish
Article numbere202305733
JournalAngewandte Chemie International Edition
Volume62
Issue number39
Early online date31 Jul 2023
Publication statusPublished - 17 Sept 2023
Externally publishedYes

Abstract

Carbohydrates are the most abundant organic material on Earth and the structural “material of choice” in many living systems. Nevertheless, design and engineering of synthetic carbohydrate materials presently lag behind that for protein and nucleic acids. Bottom-up engineering of carbohydrate materials demands an atomic-level understanding of their molecular structures and interactions in condensed phases. Here, high-resolution scanning tunneling microscopy (STM) is used to visualize at submolecular resolution the three-dimensional structure of cellulose oligomers assembled on Au(1111) and the interactions that drive their assembly. The STM imaging, supported by ab initio calculations, reveals the orientation of all glycosidic bonds and pyranose rings in the oligomers, as well as details of intermolecular interactions between the oligomers. By comparing the assembly of D- and L-oligomers, these interactions are shown to be enantioselective, capable of driving spontaneous enantioseparation of cellulose chains from its unnatural enantiomer and promoting the formation of engineered carbohydrate assemblies in the condensed phases.

Keywords

    Carbohydrate Materials, Chirality, Electrospray Ionization, Scanning Probe Microscopy, Self-Assembly

ASJC Scopus subject areas

Cite this

Visualizing Chiral Interactions in Carbohydrates Adsorbed on Au(111) by High‐Resolution STM Imaging. / Seibel, Johannes; Fittolani, Giulio; Mirhosseini, Hossein et al.
In: Angewandte Chemie International Edition, Vol. 62, No. 39, e202305733, 17.09.2023.

Research output: Contribution to journalArticleResearchpeer review

Seibel, J, Fittolani, G, Mirhosseini, H, Wu, X, Rauschenbach, S, Anggara, K, Seeberger, PH, Delbianco, M, Kühne, TD, Schlickum, U & Kern, K 2023, 'Visualizing Chiral Interactions in Carbohydrates Adsorbed on Au(111) by High‐Resolution STM Imaging', Angewandte Chemie International Edition, vol. 62, no. 39, e202305733. https://doi.org/10.1002/anie.202305733
Seibel, J., Fittolani, G., Mirhosseini, H., Wu, X., Rauschenbach, S., Anggara, K., Seeberger, P. H., Delbianco, M., Kühne, T. D., Schlickum, U., & Kern, K. (2023). Visualizing Chiral Interactions in Carbohydrates Adsorbed on Au(111) by High‐Resolution STM Imaging. Angewandte Chemie International Edition, 62(39), Article e202305733. https://doi.org/10.1002/anie.202305733
Seibel J, Fittolani G, Mirhosseini H, Wu X, Rauschenbach S, Anggara K et al. Visualizing Chiral Interactions in Carbohydrates Adsorbed on Au(111) by High‐Resolution STM Imaging. Angewandte Chemie International Edition. 2023 Sept 17;62(39):e202305733. Epub 2023 Jul 31. doi: 10.1002/anie.202305733
Seibel, Johannes ; Fittolani, Giulio ; Mirhosseini, Hossein et al. / Visualizing Chiral Interactions in Carbohydrates Adsorbed on Au(111) by High‐Resolution STM Imaging. In: Angewandte Chemie International Edition. 2023 ; Vol. 62, No. 39.
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abstract = "Carbohydrates are the most abundant organic material on Earth and the structural “material of choice” in many living systems. Nevertheless, design and engineering of synthetic carbohydrate materials presently lag behind that for protein and nucleic acids. Bottom-up engineering of carbohydrate materials demands an atomic-level understanding of their molecular structures and interactions in condensed phases. Here, high-resolution scanning tunneling microscopy (STM) is used to visualize at submolecular resolution the three-dimensional structure of cellulose oligomers assembled on Au(1111) and the interactions that drive their assembly. The STM imaging, supported by ab initio calculations, reveals the orientation of all glycosidic bonds and pyranose rings in the oligomers, as well as details of intermolecular interactions between the oligomers. By comparing the assembly of D- and L-oligomers, these interactions are shown to be enantioselective, capable of driving spontaneous enantioseparation of cellulose chains from its unnatural enantiomer and promoting the formation of engineered carbohydrate assemblies in the condensed phases.",
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