Synthesis and characterization of functionalized 4-O-methylglucuronoxylan derivatives

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.
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https://hal.archives-ouvertes.fr/hal-01365147
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Submitted on : Tuesday, September 13, 2016 - 11:28:25 AM
Last modification on : Thursday, January 11, 2018 - 6:28:09 AM

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Maud Chemin, Alex Rakotovelo, Frédérique Ham-Pichavant, Guillaume Chollet, Denilson Da Silva Perez, et al.. Synthesis and characterization of functionalized 4-O-methylglucuronoxylan derivatives . Holzforschung, De Gruyter, 2015, 69 (6), pp.713-720. ⟨10.1515/hf-2014-0290 ⟩. ⟨hal-01365147⟩

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