Next Article in Journal
Biopolymers for Hard and Soft Engineered Tissues: Application in Odontoiatric and Plastic Surgery Field
Next Article in Special Issue
Polysaccharides: The “Click” Chemistry Impact
Previous Article in Journal
Bioinspired Poly(2-oxazoline)s
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,*
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)
View Full-Text   |   Download PDF [967 KB, uploaded 24 February 2011]   |  

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 cellulose; 6-bromo-6-deoxycellulose; 6-azide-6-deoxycellulose; glycopolymers; regio-selective modifications; lectins; molecular dynamics
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Polymers EISSN 2073-4360 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert