The enzymatic synthesis of sugar amino acid esters in polar organic solvents was studied using surfactant-enzyme complexes, which were previously developed as a highly active biocatalyst in organic solvents. Of the several lipases and proteases tested, the surfactant-subtilisin complex exhibited the highest synthetic activity in pyridine. The amino acid was regioselectively introduced at the C-6 position Of D-glucose and at the C-6' of maltose by the surfactant-subtilisin complex. This biocatalyst was found to effectively catalyze the synthesis of various sugar amino acid esters in a polar organic solvent.