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    D-Xylose and L-arabinose laurate esters: Enzymatic synthesis, characterization and physico-chemical properties

    Year: 2018

    Journal: Enzyme Microb. Technol., Volume 112, MAY, page 14–21

    Authors: Meline, Thomas; Muzard, Murielle; Deleu, Magali; Rakotoarivonina, Harivony; Plantier-Royon, Richard; Remond, Caroline

    Organizations: French Region Grand Est; Grand Reims; Feder; European Regional Development Fund (ERDF); Region Grand Est

    Keywords: D-Xylose laurate esters; L-Arabinose laurate esters; Lipase; Surfactants; Biorefinery

    Efficient enzymatic synthesis of o-xylose and L-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalysed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of o-xylose or L-arabinose and vinyllaurate at 50 degrees C. In case of L-arabinose, one monoester and one diester were obtained in a 57% overall yield. A more complex mixture was produced for D-xylose as two monoesters and two diesters were synthesized in a 74.9% global yield. The structures of all these pentose laurate esters was solved. Results demonstrated that the esterification first occurred regioselectively onto the primary hydroxyl groups. Pentose laurate esters exhibited interesting features such as low critical aggregation concentrations values all inferior to 25 mu M. Our study demonstrates that the enzymatic production of L-arabinose and D-xylose-based esters represents an interesting approach for the production of green surfactants from lignocellulosic biomass-derived pentoses.
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