ORGN 41 |
| Toshitsugu Kai, Xue-Long Sun, and Elliot L. Chaikof. Department of Surgery and Bioengineering, Emory University School of Medicine, 1639 Pierce Drive, Atlanta, GA 30322 |
| Considerable current interest in the development of model biomembranes has been drawn toward the fabrication of amphiphilic lipid for a wide range of applications such as biosensors, drug delivery systems, and biofunctional surfaces. Various model compounds have been synthesized until now, but most of them have limitations in stability, structural and chemical versatility, and ease of self-assembly formation. In recent years, bolaamphiphiles have progressively gained importance because of their abilities to provide stable supramolecular structures and advanced biomaterials. Among them, bolaamphiphiles having two different polar headgroups at opposite ends of the hydrophobic core are less common mainly due to synthetic difficulties. We describe herein a new phospholipid-based asymmetric bolaamphiphile, which was synthesized via a key intermediate diester containing different protective groups, followed by selective deprotection, and esterification of lyso-PC to one terminal and amino group containing glycerol derivative to the other side. The characterization of chemical and physical properties of this bolaamphiphile will also be discussed. |
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Lipids, Biosynthesis, Enzyme Inhibitors, and Mimetics
8:00 AM-11:40 AM, Sunday, September 7, 2003 Sheraton New York -- Royal Ballroom B, Oral
Division of Organic Chemistry |