Synthesis of new sugar-based surfactants having biological applications: Key role of their self-association

Non-ionic surfactants based on sugars are of interest to both chemists and biochemists. They have potential pharmaceutical (biocompatible formulation) biochemical (extraction of membrane proteins) and medicinal applications; generally these derivatives are not readily synthesized as the starting sugars require protection. We present here routes, avoiding protection of the starting sugars, to new series of surfactants derived from lactose, glucose, gluconic or lactobionic acids. By changing the tail or the hydrophobic body bonded to the sugar heads, we have synthesized sugar-based amphiphilic compounds having (1) one chain, (2) one fluorinated chain, (3) a double chain or (4) two sugar heads (bolaamphiphilic compounds). All these compounds form aggregates in solution: direct, reverse micelles, or vesicles. Fluorinated molecules give gels in aqueous or non-aqueous media. Some of them are interesting products to extract membrane proteins or to formulate solution of hydrophobic acids to realize enzymatic reactions. Finally soluble analogs of Galcer possess activity against both HIV and Aspergillus fumigatus, a yeast responsible for opportunistic infections in AIDS patients. (C) 1997 Elsevier Science B.V .