This project is funded by the Chemical Measurement and Imaging (CMI) program in the Division of Chemistry. Professors Billiot and Billiot of Texas A&M University - Corpus Christi, Kevin Morris of Carthage College, and Yayin Fang of Howard University form a multi-institutional collaboration. The work focuses on the investigation and elucidation of the factors responsible for molecular self-assembly, and how these factors affect the ability of the self-assembled molecular structures to interact and recognize other molecules of biological importance. A variety of experimental and computational methods are used to developed Quantitative Structure Enantioselective Retention Relationships (QSERR). QSERR is then used to evaluate and compare the effectiveness of different chiral selectors for capillary electrophoretic separations. Two of the three institutions are primarily undergraduate institutions that currently do not have a master's program in chemistry. Thus, the research will be conducted at these two schools exclusively by undergraduate students. One of these is also a Hispanic Serving Institution. The third university involved in the research is an HBCU. The research serves as a tool for the PIs to recruit, train, and mentor students from underrepresented and economically challenged backgrounds and to encourage these students to pursue post baccalaureate degrees in science. <br/><br/>The proposed research is part of an ongoing, long-term multi-faceted study focusing on investigating and elucidating the factors responsible for (a) self-assembly, (b) function, (c) higher ordered structure and (d) molecular recognition of amino acid based macromolecular assemblies (AABMAs). In particular, the research will focus on examining the effects that pH, ionic strength, surfactant concentration, and type of counter-ion have on the factors mentioned above. These AABMAs are being utilized in this study as chiral pseudostationary phases in capillary electrophoresis. Thus, the major focus of these studies is to gain insights into the factors responsible for chiral recognition with this class of chiral selector. A deeper understanding of these factors will lead to enhanced chiral separations and improved pseudostationary phases. Understanding such interactions is not only important in the development of chiral recognition media but also in the optimization of the separation conditions. In addition, since enantiorecognition of the systems under study are amino acids, the knowledge gained from these studies will be potentially transferable to other amino acid based systems such as proteins.