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

A simple and flexible chemoenzymatic route for the preparation of a wide ra nge of dimeric (gemini) and trimeric mono- and disaccharide-based surfactan ts was developed. The synthesis relies on the use of enzymes for regioselec tive introduction of fatty acids into carbohydrate moieties. Several struct ures were prepared containing xylose, glucose, galactose, and lactose, conn ected via different hydroxyl groups in the sugar molecules or, alternativel y, via the OH group of 2-hydroxytetradecanoic acid used as a hydrophobic mo iety for the surfactant. Paper no. JSD1096 in JSD 2, 293-302 (July 1999).