FARE laboratory, Chaire AFERE, Université de Reims-Champagne-Ardenne, INRA, 51686 Reims Cedex, France.
Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, Université de Reims Champagne-Ardenne, 51687 Reims Cedex, France.
Enzyme Microb Technol. 2018 May;112:14-21. doi: 10.1016/j.enzmictec.2018.01.008. Epub 2018 Feb 4.
Efficient enzymatic synthesis of d-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 d-xylose or l-arabinose and vinyllaurate 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.
通过固定化南极假丝酵母脂肪酶 B 作为生物催化剂，在有机介质中，于 50°C 下，用木糖或阿拉伯糖和乙烯基月桂酸酯进行酯交换反应，可有效地合成 d-木糖和 l-阿拉伯糖的月桂单酯和双酯。对于 l-阿拉伯糖，可获得 57%的总收率的一种单酯和一种双酯。对于 d-木糖，则生成了更复杂的混合物，两种单酯和两种双酯的总收率为 74.9%。所有这些戊糖月桂酸酯的结构都得到了解决。结果表明，酯化首先是在伯羟基上发生区域选择性的。戊糖月桂酸酯具有有趣的特性，如低临界聚集浓度值均低于 25μM。我们的研究表明，酶法生产基于 l-阿拉伯糖和 d-木糖的酯类是从木质纤维素生物质衍生的戊糖生产绿色表面活性剂的一种很有前途的方法。
