Faculty Advisor(s)
John P. Morgan
Files
Download Poster (902 KB)
Abstract
Native Chemical Ligation (NCL) is a process by which smaller peptides can be linked together to form larger peptides and proteins, but the preparation of necessary thioester starting materials often relies on hazardous reagents. We report a greener synthesis of S-(4- nitrophenyl) N-acetylphenylalaninethioate, building upon the methodology reported by Raines et al.1 This literature synthesis uses N,N-dimethylformamide (DMF) as solvent in the final thioester coupling step to accommodate the limited solubility of N-acetylphenylalanine in less polar solvents. However, DMF is a known reproductive toxin and environmental hazard. Our research demonstrates that acidic water serves as a highly effective, benign alternative to DMF for this coupling reaction, without significant concomitant hydrolysis of the thioester product. Our modification not only enhances the environmental profile of the synthesis but also simplifies the isolation of the desired thioester product. By replacing hazardous organic solvents with water, we provide a more sustainable and efficient route to essential starting materials for NCL applications.
Publication Date
2026
Document Type
Poster
Department
Chemistry & Biochemistry
Keywords
green chemistry, acetylation, native chemical ligation, thioester, peptide
Disciplines
Amino Acids, Peptides, and Proteins | Chemistry | Organic Chemicals | Other Chemicals and Drugs | Pharmaceutical Preparations | Physical Sciences and Mathematics
Recommended Citation
Marley, Kaitlyn S.; Werle, Hannah M.; and Morgan, John P., "Green Modification of a Coupling Reaction Between N-Acetylated Amino Acids and p-Nitrothiophenol" (2026). SURF Posters 2026. 5.
https://digitalcommons.misericordia.edu/surf2026/5
Included in
Amino Acids, Peptides, and Proteins Commons, Chemistry Commons, Organic Chemicals Commons, Other Chemicals and Drugs Commons, Pharmaceutical Preparations Commons