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

Seibel, Johannes 1; Fittolani, Giulio; Mirhosseini, Hossein; Wu, Xu; Rauschenbach, Stephan; Anggara, Kelvin; Seeberger, Peter H.; Delbianco, Martina; Kühne, Thomas D.; Schlickum, Uta; Kern, Klaus
1 Institut für Physikalische Chemie (IPC), Karlsruher Institut für Technologie (KIT)

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.


Verlagsausgabe §
DOI: 10.5445/IR/1000161995
Veröffentlicht am 11.09.2023
Originalveröffentlichung
DOI: 10.1002/anie.202305733
Scopus
Zitationen: 8
Web of Science
Zitationen: 5
Dimensions
Zitationen: 7
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Physikalische Chemie (IPC)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 25.09.2023
Sprache Englisch
Identifikator ISSN: 1433-7851, 0570-0833, 1521-3773
KITopen-ID: 1000161995
Erschienen in Angewandte Chemie - International Edition
Verlag John Wiley and Sons
Band 62
Heft 39
Seiten Art.-Nr.: e202305733
Vorab online veröffentlicht am 22.08.2023
Schlagwörter Carbohydrate Materials, Chirality, Scanning Probe Microscopy, Self-Assembly, Electrospray Ionization
Nachgewiesen in Dimensions
Web of Science
Scopus
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