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Keywords = 6-bromo-6-deoxycellulose

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20 pages, 967 KiB  
Article
Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity
by Kaori Negishi, Yoichi Mashiko, Erika Yamashita, Atsushi Otsuka and Teruaki Hasegawa
Polymers 2011, 3(1), 489-508; https://doi.org/10.3390/polym3010489 - 24 Feb 2011
Cited by 30 | Viewed by 11136
Abstract
b-1,4-Glucans having oligosaccharide appendages (O-/N-linked b-maltoside and O-/N-linked b-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 [...] Read more.
b-1,4-Glucans having oligosaccharide appendages (O-/N-linked b-maltoside and O-/N-linked b-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. Full article
(This article belongs to the Collection Polysaccharides)
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