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Systematic hydrogen-bond manipulations to establish polysaccharide structure–property correlations

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Yu,  Yang
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Tyrikos-Ergas,  Theodore
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Zhu,  Yuntao
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Fittolani,  Giulio
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Bordoni,  Vittorio
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Singhal,  Ankush
Andrea Grafmüller, Theorie & Bio-Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Fair,  Richard J.
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Grafmüller,  Andrea
Andrea Grafmüller, Theorie & Bio-Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Delbianco,  Martina
Martina Delbianco, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Yu, Y., Tyrikos-Ergas, T., Zhu, Y., Fittolani, G., Bordoni, V., Singhal, A., et al. (2019). Systematic hydrogen-bond manipulations to establish polysaccharide structure–property correlations. Angewandte Chemie International Edition, 58(37), 13127-13132. doi:10.1002/anie.201906577.


Cite as: https://hdl.handle.net/21.11116/0000-0004-627D-2
Abstract
A dense hydrogen bond network is responsible for the mechanical and structural properties of polysaccharides. Random derivatization alters thematerial bulk properties by disrupting the hydrogen bonds, but obstructs detailed structure-function correlations. We prepare well-defined unnatural oligosaccharidesincludingmethylated, deoxygenated, deoxyfluorinated, as well as carboxymethylated cellulose and chitin analogueswith full control over degree and patternof substitution.Molecular dynamics simulationsand crystallographic analysis showhow distinct H-bond modifications drastically affect thesolubility, aggregation behaviour, and crystallinityof carbohydratematerials. This systematic approachto establishingdetailed structure-propertycorrelations will guide the synthesis of novel, tailor-made carbohydrate materials.