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

Authors
  • negishi, kaori
  • mashiko, yoichi
  • yamashita, erika
  • otsuka, atsushi
  • hasegawa, teruaki
Publication Date
Feb 24, 2011
Identifiers
DOI: 10.3390/polym3010489
OAI: oai:mdpi.com:/2073-4360/3/1/489/
Source
MDPI
Keywords
Language
English
License
Green
External links

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.

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