| dc.description.abstract | This work describes the synthesis of a 24-atom, threonine-rich macrocycle homodimer, T-T. Syntheses of macrocycles are of interest due to their potential applications as drugs. If the synthesis design allows for a wide variety of different groups to be incorporated without affecting the structure itself, classical drug design strategies can be adopted. The benefits of macrocycles derive from their large and flexible structures that can adopt different conformations. This flexibility is important when the macrocycle is required to present either hydrophilic or hydrophobic surfaces when it is inside and outside the cell or crossing the membrane, respectively. The synthesis of T-T is done in three steps and relied on making changes to a previously studied macrocycle synthesis pathway. First, a threonine acid intermediate is prepared by substituting a triazine ring with dimethyl amine, a t-butyl protected threonine and a BOC-protected hydrazine. Then, the acid is reacted to create the threonine acetal monomer. The final step involves treating the monomer with acid to yield the homodimer, T-T. The macrocycle and its intermediates were purified through column chromatography and characterized via 1H NMR, 13C NMR, COSY NMR, rOesy NMR, and HSQC NMR. What emerges from these studies is the three-dimensional shape of T-T. 1H NMR and 13C NMR were also used to characterize the acid intermediate and the acetal monomer. Mass spectrometry also corroborated these assignments. This research adds to a growing library of similar macrocycles that vary in amino acid in the position of threonine with the eventual goal of creating a library of macrocycles for future research in the area of synthetic drug design. Separately, during the spring semester of the 2020-2021 academic year at Texas Christian University a group of 12 undergraduate students participated in a group project given the title Introduction to Research. These students chose to participate in this project after their organic chemistry II laboratory course was moved to an online format two weeks into the start of the semester. The goal of the project was to provide undergraduate students the opportunity to participate in faculty led organic chemistry research which would supplement their laboratory course being moved online. This review seeks to cover what the undergraduate students were able to accomplish over the course of the semester while meeting weekly to work on this project. Additionally, a survey was given to the students after they completed the semester in order to get their opinion on how the structure of the course operated as well as areas which could be improved if the opportunity was offered to students again in the future. The opinions received from the survey demonstrated that the undergraduate students felt that the experience was extremely positive with only a few areas in which the operations could have been improved. This review takes the summary of student activities through this project as well as their perspectives gained through the survey in order to provide guidelines on how a similarly styled opportunity could be offered in the future as a class course at TCU. | |
