Date of Graduation
Summer 2024
Degree
Master of Science in Chemistry
Department
Chemistry & Biochemistry
Committee Chair
Keiichi Yoshimatsu
Abstract
In this study, I optimized the amount of solvent, dimethylformamide, and the coupling reagent equivalencies of N,N’-diisopropylcarbodiimide and either 1-hydroxybenzotriazole or Oxyma Pure for small-scale solid-phase peptide synthesis. The synthesis of truncated and full-length Leu-enkephalin amides were chosen as the model system for this study. In order to analyze the yield and purity of crude peptide products, I developed LC-MS methods. Thereafter, I investigated the utility of in situ Fmoc removal method to reduce the solvent consumption in solid-phase peptide synthesis using N,N’-diisopropylcarbodiimide and 1-hydroxybenzotriazole. As a control experiment, I reproduced the previously reported experiment on the use of in situ Fmoc removal method using N,N’-diisopropylcarbodiimide and Oxyma Pure. The results showed that the yield and purity of the obtained peptide products were comparable when these two sets of reagents were used as the coupling reagents. These results demonstrate that the in situ Fmoc removal method is not limited to N,N’-diisopropylcarbodiimide and Oxyma Pure.
Keywords
solid-phase peptide synthesis, dimethylformamide, in situ fmoc removal, diisopropylcarbodiimide, benzotriazole, oxyma, green chemistry
Subject Categories
Environmental Chemistry | Medicinal-Pharmaceutical Chemistry | Organic Chemistry | Polymer Chemistry
Copyright
© Alexander M. Babel
Recommended Citation
Babel, Alexander M., "Comparative Study on Different Fmoc Solid-Phase Peptide Synthesis Protocols Towards Reduced Solvent Consumption and Improved Efficiency" (2024). MSU Graduate Theses. 3996.
https://bearworks.missouristate.edu/theses/3996
Open Access
Included in
Environmental Chemistry Commons, Medicinal-Pharmaceutical Chemistry Commons, Organic Chemistry Commons, Polymer Chemistry Commons
