Details
| Original language | English |
|---|---|
| Article number | e202305733 |
| Journal | Angewandte Chemie International Edition |
| Volume | 62 |
| Issue number | 39 |
| Early online date | 31 Jul 2023 |
| Publication status | Published - 17 Sept 2023 |
| Externally published | Yes |
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
- Chemistry(all)
- General Chemistry
- Chemical Engineering(all)
- Catalysis
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In: Angewandte Chemie International Edition, Vol. 62, No. 39, e202305733, 17.09.2023.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Visualizing Chiral Interactions in Carbohydrates Adsorbed on Au(111) by High‐Resolution STM Imaging
AU - Seibel, Johannes
AU - Fittolani, Giulio
AU - Mirhosseini, Hossein
AU - Wu, Xu
AU - Rauschenbach, Stephan
AU - Anggara, Kelvin
AU - Seeberger, Peter H.
AU - Delbianco, Martina
AU - Kühne, Thomas D.
AU - Schlickum, Uta
AU - Kern, Klaus
N1 - Publisher Copyright: © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
PY - 2023/9/17
Y1 - 2023/9/17
N2 - 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.
AB - 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.
KW - Carbohydrate Materials
KW - Chirality
KW - Electrospray Ionization
KW - Scanning Probe Microscopy
KW - Self-Assembly
UR - http://www.scopus.com/inward/record.url?scp=85168627304&partnerID=8YFLogxK
U2 - 10.1002/anie.202305733
DO - 10.1002/anie.202305733
M3 - Article
VL - 62
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1521-3773
IS - 39
M1 - e202305733
ER -