Regioselective synthesis of dimeric (gemini) and trimeric sugar-based surfactants

A simple and flexible chemoenzymatic route for the preparation of a wide range of dimeric (gemini) and trimeric mono- and disaccharide-based surfactants was developed. The synthesis relies on the use of enzymes for regioselective introduction of fatty acids into carbohydrate moieties. Several structures were prepared containing xylose, glucose, galactose, and lactose, connected via different hydroxyl groups in the sugar molecules or, alternatively, via the OH group of 2-hydroxytetradecanoic acid used as a hydrophobic moiety for the surfactant. Paper no. JSD1096 in JSD 2, 293-302 (July 1999).