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Synthesis and characterization of functionalized 4-O-methylglucuronoxylan derivatives

  • Maud Chemin , Alex Rakotovelo , Frédérique Ham-Pichavant , Guillaume Chollet , Denilson da Silva Perez , Michel Petit-Conil , Henri Cramail EMAIL logo and Stéphane Grelier EMAIL logo
Published/Copyright: March 4, 2015
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Abstract

The purpose of this study was to design new biomaterials based on functionalized xylan derivatives. In one approach, 4-O-methylglucuronoxylan (MGX) of beechwood was oxidized by sodium periodate (NaIO4). A ratio of 0.2 NaIO4/xylose leads to a degree of oxidation of 0.15 with 75% yield. Then, the oxidized MGX aldehyde was submitted to reductive amination reaction with benzylamine, and as a result, the xylan backbone was effectively grafted with benzyl groups with a degree of substitution of 0.11. In another approach, controlled sulfuric acidic hydrolysis of MGX was performed to get well-defined xylooligosaccharides (XOS). Then, the reductive amination reaction of the XOS aldehyde functions was performed with allylamine or 2-aminoethylazide to graft the chain ends with an allyl or an azide function, respectively. The proposed methods can open a route to the design of new functional biomaterials.


Corresponding authors: Henri Cramail, Univ. Bordeaux, LCPO, UMR 5629, 16 av. Pey Berland, F-33607 Pessac, France, e-mail: , and Stéphane Grelier, Univ. Bordeaux, LCPO, UMR 5629, 16 av. Pey Berland, F-33607 Pessac, France, e-mail: ; and CNRS, LCPO, UMR 5629, 16 av. Pey Berland, Pessac, F-33607 Pessac, France

Acknowledgments

This work is financially supported by the Aquitaine Council, ITERG, FCBA, and ANR-10-EQPX-16 XYLOFOREST. The authors thank C. Absalon [CESAMO, Institut des Sciences Moléculaires, Université de Bordeaux, Talence (33), France] for MALDI-TOF experiments.

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Received: 2014-10-6
Accepted: 2015-2-4
Published Online: 2015-3-4
Published in Print: 2015-8-1

©2015 by De Gruyter

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