Synthesis and preliminary biochemical assessment of ethyl-terminated perfluoroalkylamine oxide surfactants

• Published in: Bioorganic & medicinal chemistry letters 2002-06, Vol.12 (12), p.1587-1590
• Main Authors: Chaudier, Yann, Zito, Francesca, Barthélémy, Philippe, Stroebel, David, Améduri, Bruno, Popot, Jean-Luc, Pucci, Bernard
• Format: Article
• Language: English
• Subjects: Biological and medical sciences; Biotechnology; Chemistry; Cytochrome b Group - metabolism; Cytochrome b6f Complex; Exact sciences and technology; Fluorocarbons - chemical synthesis; Fluorocarbons - metabolism; Fundamental and applied biological sciences. Psychology; General and physical chemistry; Methods. Procedures. Technologies; Others; Surface physical chemistry; Surface-Active Agents - chemical synthesis; Surface-Active Agents - metabolism; Surface-active agents: properties; Various methods and equipments
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(02)00242-1

The synthesis and usefulness in membrane biochemistry of a new class of surfactants have been investigated. 1-Ethyl-2-dimethylamine oxide polar heads were grafted onto a hydrocarbon, a fluorocarbon or an ethyl-capped fluorocarbon hydrophobic tail. The ability of the resulting surfactants to extract and/or to stabilize in aqueous solution a test membrane protein, cytochrome b 6 f, was evaluated. While it is not a detergent, the hemifluorinated derivative efficiently kept purified cytochrome b 6 f soluble, native and functional. The data suggest that alkyl-capped fluorocarbon surfactants provide an interesting alternative to classical detergents for handling membrane proteins in aqueous solutions under non-dissociating conditions. The synthesis of ethyl-terminated perfluoroalkylamine oxide surfactants is reported. The efficiency of these new surfactants in maintaining membrane proteins soluble in aqueous solution was assayed.