Journal
POLYMERS
Volume 3, Issue 1, Pages 489-508Publisher
MDPI AG
DOI: 10.3390/polym3010489
Keywords
cellulose; 6-bromo-6-deoxycellulose; 6-azide-6-deoxycellulose; glycopolymers; regio-selective modifications; lectins; molecular dynamics
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [18750103]
- Special Research Fund of Toyo University
- Grants-in-Aid for Scientific Research [18750103] Funding Source: KAKEN
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beta-1,4-Glucans having oligosaccharide appendages (O-/N-linked. beta-maltoside and O-/N-linked. beta-lactoside) at 6C positions of all repeating units can be readily prepared from cellulose through a two step strategy composed of: (1) regio-selective and quantitative bromination/azidation to afford 6-azido-6-deoxycellulose; and (2) the subsequent Cu+-catalyzed coupling with oligosaccharides having terminal alkyne. The resultant cellulose derivatives showed improved water solubility in comparison to native cellulose; they, however, bound to carbohydrate-binding proteins in a rather non-specific manner. Molecular dynamics calculations revealed that these properties are attributable to rigid sheet-like structures of the cellulose derivatives and the subsequent exposure of their hydrophobic moieties to solvents.
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