Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity

Kaori Negishi, Yoichi Mashiko, Erika Yamashita, Atsushi Otsuka, Teruaki Hasegawa
2011 Polymers  
-1,4-Glucans having oligosaccharide appendages (O-/N-linked -maltoside and O-/N-linked -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
more » ... n 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.
doi:10.3390/polym3010489 fatcat:gg25lqxvtrfsppe7ccrkay6sja