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

• Published in: Enzyme and Microbial Technology
• Main Authors: Méline, Thomas, Muzard, Murielle, Deleu, Magali, Rakotoarivonina, Harivony, Plantier-Royon, Richard, Rémond, Caroline
• Other Authors: Fractionnement des AgroRessources et Environnement (FARE), Université de Reims Champagne-Ardenne (URCA)-Institut National de la Recherche Agronomique (INRA), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Liège
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2018
• Subjects: Biorefinery; D-Xylose laurate esters; L-Arabinose laurate esters; Lipase; Surfactants; [SDV]Life Sciences [q-bio]; Antarc*; Antarctica
• Online Access: https://hal.archives-ouvertes.fr/hal-01763242; https://doi.org/10.1016/j.enzmictec.2018.01.008

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.