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• Negishi, K
• Mashiko, Y
• Yamashita, E
• Otsuka, A
• Hasegawa, T
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• Negishi, K
• Mashiko, Y
• Yamashita, E
• Otsuka, A
• Hasegawa, T
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• Negishi, K
• Mashiko, Y
• Yamashita, E
• Otsuka, A
• Hasegawa, T

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Polymers 2011, 3(1), 489-508; doi:10.3390/polym3010489

Article

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

Kaori Negishi ^1,2 , Yoichi Mashiko ^1,2 , Erika Yamashita ³ , Atsushi Otsuka ^1,2  and Teruaki Hasegawa ^2,3,*

¹ Graduate School of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Japan ² Bio-Nano Electronics Research Centre, Toyo University, 2100 Kujirai, Kawagoe 350-8585, Japan ³ Department of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Japan

* Author to whom correspondence should be addressed.

Received: 6 January 2011 / Accepted: 6 February 2011 / Published: 24 February 2011

(This article belongs to the Special Issue Click Chemistry in Polymer Science)

Download PDF Full-Text [967 KB, uploaded 24 February 2011 11:06 CET]

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 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.

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

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