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

1,2, 1,2, 3, 1,2 and 2,3,* email
Received: 6 January 2011; Accepted: 6 February 2011 / Published: 24 February 2011
(This article belongs to the Special Issue Click Chemistry in Polymer Science)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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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.

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