A simple procedure for the regioselective synthesis of fatty acid esters of maltose, leucrose, maltotriose and n-dodecyl maltosides

The enzymatic acylation of several di- and trisaccharides with acyl donors ranging from 8 to 18 carbon atoms was carried out by transesterification wi th the corresponding vinyl esters. The reaction was performed in 2-methyl-2 -butanol/dimethylsulfoxide mixtures using the lipase from Humicola lanugino sa (immobilized on Celite). Maltose, maltotriose and n-dodecyl maltosides w ere specifically acylated in the primary hydroxyl of the non-reducing-end g lucose moiety; the acylation of leucrose occurred preferentially in the pri mary hydroxyl of the glucose ring. (C) 2000 Elsevier Science Ltd. All right s reserved.