D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties

Thomas Méline (1) , Murielle Muzard (1) , Magali Deleu (2) , Harivony Rakotoarivonina (1) , Richard Plantier-Royon (1) , Caroline Rémond (1)

1 URCA - Université de Reims Champagne-Ardenne
2 Université de Liège - Gembloux

Efficient enzymatic synthesis of D-xylose and L-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalyzed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of D-xylose or L-arabinose and vinyl laurate at 50 °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 µM. 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.

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

Domaines: Sciences du Vivant [q-bio]

Thomas Méline, Murielle Muzard, Magali Deleu, Harivony Rakotoarivonina, Richard Plantier-Royon, et al.. D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties. Enzyme and Microbial Technology, 2018, 112, pp.14-21. ⟨10.1016/j.enzmictec.2018.01.008⟩. ⟨hal-02962676⟩