"Development of Synthesis Strategies for the
Preparation of Cyclic Glucotetrasaccharide (CTS)
Based Gemini Amphiphiles"

Gemini surfactants, (geminis, the common name for "bis-surfactants") constitute a new class of amphiphilic molecules and are composed of two hydrophobic, hydrocarbon chains and two hydrophilic head groups connected by a spacer. Thus, instead of having a single hydrocarbon tail connected to an ionic or polar head group (as in a conventional surfactant), geminis have the arrangement shown below (Menger and Mbadugha).

Research over the last decade to synthesize and characterize Gemini surfactants, consequently unveiling the distinct behavior and properties exhibited by this new class of amphiphilic molecules, has led to increased interest by industrial groups within the last few years due to their promising applications in diverse areas, e.g., skin care, antibacterial regimens, biological membranes, construction of high-porosity materials, analytical separations, and solubilization processes (Menger and Keiper 2000). Consequently, organic chemists have become interested in synthesizing new gemini surfactant compounds that could potentially display properties of greater interest, uniqueness, and value, such as the cyclic tetrasaccharide (CTS) based Gemini. CTS consist of four sugar (tetrasaccharide) moieties cyclically arranged to form a gemini. CTS "from a structural perspective, is ideal for incorporation into a gemini motif based on its symmetry and susceptibility for substitution at the two primary hydroxyl positions" (Mbadugha, 2001).

The ultimate goal of this research is to discover a feasible synthetic route for gemini surfactants containing a cyclic tetrasaccharide. Based on previous literature (Menger and Mbadugha, 2001) it is likely that this can be achieved by using trehalose, a disaccharide analog of CTS. Trehalose is expected to have chemically similar behavior to CTS, and is commercially, readily available. As a result, the specific aim of the synthesis I am conducting is to prepare a trehalose gemini by attaching long chains to primary hydroxyl positions on trehalose, via amino linkages, in hopes that a similar synthetic protocol could be exploited in synthesizing CTS geminis.