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Publication Date
2017-5
First Advisor
David Bickar
Document Type
Honors Project
Degree Name
Bachelor of Arts
Department
Chemistry
Keywords
Oxazoles, Peptide, Antibiotic, Ion channel design, Peptides-Synthesis, Antibiotics
Abstract
Antibiotic resistance is a rapidly growing problem in the past seventy years. Over the past year over 2 million people were diagnosed with antibacterial resistant infections, at least 23,000 of whom died from their infections (Silva, 2016). However, over recent years a promising new class of antibiotics has emerged, known as cyclic antimicrobial peptides (AMP). These structures indirectly attack the bacterial cells by forming pores in the cell walls (Straus, 2006).
Recent studies have shown that small heterocyclic groups in macrocyclic structures can improve their resistance to proteolytic degradation. For the purposes of this study oxazole rings were incorporated into the design because in addition to inhibiting proteolysis, oxazole groups are themselves chemically stable and therapeutically active. (Kelleher, 1998)
In this study, a novel peptidic structure was designed and synthesized. Through several syntheses a successful synthetic strategy was developed to obtain this compound.
The designed molecule was obtained in a 45% yield. For each step of the synthesis the identity of the product was characterized using 1 H and 13 C NMR, IR, and Mass Spectrometry. Although the final product proved to be extremely insoluble, it was determined to be an effective ion channel upon addition to a synthetic bilayer system.
Language
English
Recommended Citation
Graham-O'Regan, Katherine Anne, "Design and synthesis of a novel cyclic oxazole pseudopeptide" (2017). Honors Project, Smith College, Northampton, MA.
https://scholarworks.smith.edu/theses/1822
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Comments
113 pages : illustrations (some color). Includes bibliographical references (pages 106-113)