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

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)
PDF Full-text 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

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

Negishi, K.; Mashiko, Y.; Yamashita, E.; Otsuka, A.; Hasegawa, T. Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity. Polymers 2011, 3, 489-508.

AMA Style

Negishi K, Mashiko Y, Yamashita E, Otsuka A, Hasegawa T. Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity. Polymers. 2011; 3(1):489-508.

Chicago/Turabian Style

Negishi, Kaori; Mashiko, Yoichi; Yamashita, Erika; Otsuka, Atsushi; Hasegawa, Teruaki. 2011. "Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity." Polymers 3, no. 1: 489-508.

Polymers EISSN 2073-4360 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert