Synthesis and Properties of New Glucocationic Surfactants:  Model Structures for Marking Cationic Surfactants with Carbohydrates

• Published in: Journal of organic chemistry 2005-11, Vol.70 (24), p.9857-9866
• Main Authors: Quagliotto, Pierluigi, Viscardi, Guido, Barolo, Claudia, D'Angelo, Domenico, Barni, Ermanno, Compari, Carlotta, Duce, Elenia, Fisicaro, Emilia
• Format: Article
• Language: English
• Subjects: Carbohydrate Conformation; Carbohydrates - chemistry; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Cations - chemical synthesis; Cations - chemistry; Chemistry; Exact sciences and technology; Models, Molecular; Monosaccharides - chemical synthesis; Monosaccharides - chemistry; Organic chemistry; Preparations and properties; Stereoisomerism; Surface Tension; Surface-Active Agents - chemical synthesis; Surface-Active Agents - chemistry
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo051579s

In this work, we report the synthesis of a new series of glucocationic surfactants, a class of surfactants we introduced very recently. The preparation of the surfactants is based on the synthesis of the 2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside, whose preparation was studied in order to improve yields and stereoselectivity of this key intermediate. These glucocationic amphiphiles were prepared and studied as a model of cationic surfactants marked with a carbohydrate moiety. The use of carbohydrates as markers on cationic lipids was recently introduced to induce recognition by specific receptors, present on the surface of cell membranes. The chemicophysical characterization of these model structures can give more insight on the aggregation behavior. Conductivity and surface tension measurements were performed in order to characterize the compounds from the amphiphilic point of view. The results showed a different effect of the glucosidic moiety on the cmc value with respect to the glucopyridinium cationic surfactants. The surfactants also showed the tendency to form premicellar aggregates in solution when the hydrophobicity is raised.