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Poster
Synthesis of an unsymmetrical polyamine
University of West Florida Libraries
Summer Undergraduate Research Program (University of West Florida, Pensacola, Florida, 2021)
2021
Abstract
Macrocylic polyamines serve as ligands to coordinate with metal ions and are commonly used to mimic the active sites of enzymes. Our goal was to synthesize the intermediate of one such polyamine, namely, 1,4,8-Triazacycloundecane (TACU), in hopes of obtaining greater understanding of the low yield of TACU. TACU is an intermediate reagent that will be used as a scaffold to mimic the active sites of physiologically significant enzymes such as carboxypeptidase and thermolysin. The synthesis of the desired guanidinium intermediate was performed in one step. In that step, Hexahydropyrimidopyrimidine underwent a bimolecular nucleophilic substitution reaction (SN2) with the ditosylate 1,2-bis(tosyloxy)ethane by stirring at room temperature for 48 hours resulting in a tricyclic salt of a carbocation intermediate at the
most centered carbon in the molecule. Such an unsymmetrical polyamine will help in understanding its role in the synthesis, structure and function of an enzyme mimic.
This intermediate was reduced by addition of a mild reducing agent (sodium borohydride) and stirring for another 24 hours to form an orthoamide. In the second step, the orthoamide was hydrolyzed to form TACU. The product was confirmed using nuclear magnetic resonance spectroscopy (1H NMR and 13C NMR) and gas chromatography-mass spectrometry (GC-MS).
Details
- Title
- Synthesis of an unsymmetrical polyamine
- Resource Type
- Poster
- Event
- Summer Undergraduate Research Program (University of West Florida, Pensacola, Florida, 2021)
- Contributors
- Dr. Ajay R. Lajmi (Faculty Mentor)
- Publisher
- University of West Florida Libraries; Argo Scholar Commons
- Format
- pdf
- Copyright
- Permission granted to the University of West Florida Libraries to digitize and/or display this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires the permission of the copyright holder.
- Identifiers
- 99380090780606600
- Academic Unit
- Summer Undergraduate Research Program 2021
- Language
- English