Issue 42, 2022

Deoxyfluorination tunes the aggregation of cellulose and chitin oligosaccharides and highlights the role of specific hydroxyl groups in the crystallization process

Abstract

Cellulose and chitin are abundant structural polysaccharides exploited by nature in a large number of applications thanks to their crystallinity. Chemical modifications are commonly employed to tune polysaccharide physical and mechanical properties, but generate heterogeneous mixtures. Thus, the effect of such modifications is not well understood at the molecular level. In this work, we examined how deoxyfluorination (site and pattern) impact the solubility and aggregation of well-defined cellulose and chitin oligomers. While deoxyfluorination increased solubility in water and lowered the crystallinity of cellulose oligomers, chitin was much less affected by the modification. The OH/F substitution also highlighted the role of specific hydroxyl groups in the crystallization process. This work provides guidelines for the design of cellulose- and chitin-based materials. A similar approach can be imagined to prepare cellulose and chitin analogues capable of withstanding enzymatic degradation.

Graphical abstract: Deoxyfluorination tunes the aggregation of cellulose and chitin oligosaccharides and highlights the role of specific hydroxyl groups in the crystallization process

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Paper
Submitted
02 9月 2022
Accepted
12 10月 2022
First published
13 10月 2022
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2022,20, 8228-8235

Deoxyfluorination tunes the aggregation of cellulose and chitin oligosaccharides and highlights the role of specific hydroxyl groups in the crystallization process

G. Fittolani, S. Djalali, M. A. Chaube, T. Tyrikos-Ergas, M. C. S. Dal Colle, A. Grafmüller, P. H. Seeberger and M. Delbianco, Org. Biomol. Chem., 2022, 20, 8228 DOI: 10.1039/D2OB01601J

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