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

Polymers

Kaori Negishi²  Yoichi Mashiko²  Erika Yamashita¹  Atsushi Otsuka² 

[1] Department of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Japan;Graduate School of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Japan

关键词: cellulose;    6-bromo-6-deoxycellulose;    6-azide-6-deoxycellulose;    glycopolymers;    regio-selective modifications;    lectins;    molecular dynamics;   

DOI  :  10.3390/polym3010489

来源: mdpi

【 摘 要 】

β-1,4-Glucans having oligosaccharide appendages (O-/N -linked β-maltoside and O-/N -linked β -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.

【 授权许可】

CC BY   
© 2011 by the authors; licensee MDPI, Basel, Switzerland.