{"@context":"http://iiif.io/api/presentation/2/context.json","@type":"sc:Manifest","@id":"https://iiif.quartexcollections.com/berry/iiif/a86e3f85-3e43-4c59-bc5c-adc4e88e6d70/manifest","label":"SimpsonAbigail_2025_Honors","metadata":[{"label":"Identifier","value":"SimpsonAbigail_2025_Honors"},{"label":"Committee Chair","value":["Savannah Post"]},{"label":"Degree","value":["Bachelor of Science"]},{"label":"Project Type","value":["Thesis"]},{"label":"Research Funding Link","value":"Learn more about <a href=\"https://berry.edu/academics/faculty-resources/undergraduate-research/student-grants\" target=\"_blank\">student grants</a> and <a href=\"https://berry.edu/academics/faculty-resources/undergraduate-research/summer-research\" target=\"_blank\"> summer research. </a>"},{"label":"Research Funding","value":["Student Presentation Travel Fund","Summer Undergraduate Research Fellowship"]},{"label":"Author Supplied Keywords","value":"Organic Chemistry; Synthetic Chemistry; Methodology; Total Synthesis; Antimicrobials; Biochemistry"},{"label":"Author","value":["Abigail B. Simpson"]},{"label":"Department","value":["Chemistry and Biochemistry"]},{"label":"School","value":["School of Mathematical and Natural Sciences"]},{"label":"Subject","value":["Biochemistry","Antimicrobials","Total Synthesis","Methodology","Synthetic Chemistry","Organic Chemistry"]},{"label":"Access Restrictions","value":["immediate unrestricted access"]},{"label":"Rightsholder","value":["Abigail B. Simpson"]},{"label":"Rights Link","value":"<a href=\"https://rightsstatements.org/page/InC/1.0/?language=en\" target=\"_blank\"> In Copyright</a>"},{"label":"Rights","value":["In Copyright"]},{"label":"Decade","value":["2020s"]},{"label":"Type","value":["Text"]},{"label":"Holding Institution","value":["Berry College"]},{"label":"Extent","value":"52 pages"},{"label":"Medium","value":["theses"]},{"label":"Publisher","value":["Berry College"]},{"label":"Language (DLG)","value":["eng"]},{"label":"Language","value":["English"]},{"label":"Format","value":["application/pdf"]},{"label":"Description","value":"Cystobactamids are a natural family of compounds with significant antibacterial properties that provide a new approach to the growing problem of antibiotic resistance. One unique, naturally occurring tripeptide structure known as cystobactamid-507 stands as a compound of interest for optimization as an antibacterial agent. Cystobactamid-507 and its synthetic derivatives display in-vitro inhibitory activity against DNA gyrase but fail to inhibit gram-negative bacteria directly. We hypothesize that this is due to an inability to enter the cell, in which the substitution of longer alkoxy sidechains could promote the molecule's hydrophobic interactions with targeted bacterial cell membranes. To test this hypothesis, we have synthesized two cystobactamid analogs with octyl alkoxy chains for further biological evaluation. During these synthetic efforts, significant challenges were encountered during a key amide coupling reaction between two of the aryl rings. These issues consisted of poor percent yields (≤ 30%) and tedious/inconsistent purifications, diminishing the overall yield and ability to obtain sufficient quantities for biological assays. A variety of amide coupling conditions from the literature were attempted using our substrates with limited success, but overall acid-chloride mediated couplings showed the most promise. As such, we set out to optimize the highest yielding literature procedure (still ~30%) within our system. Through meticulous screening of solvents, bases, temperatures, and other reaction conditions, we have identified an optimized procedure with drastic percent yield improvement from ~30% to 94% with no column purification required."},{"label":"Date","value":"December 12 2025"},{"label":"Date (Filter)","value":"D:12 M:12 Y:2025"},{"label":"Creator","value":["Abigail B. Simpson"]},{"label":"Title","value":"Synthesis and Biological Evaluation of Octyl Alkoxy Cystobactamid-507 Derivatives & Synthetic Optimization of Amide Coupling Reaction"},{"label":"Faculty Advisor","value":["Mark Turlington"]},{"label":"Major","value":["Chemistry"]}],"description":"Synthesis and Biological Evaluation of Octyl Alkoxy Cystobactamid-507 Derivatives & Synthetic Optimization of Amide Coupling 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