Synthesis of Oxidized Penicillin G Derivatives
The widespread use of antibiotics is polluting water systems that are giving rise to antibiotic resistant bacteria. Conventional water treatments are not effective in removing antibiotics from the water, which flow into ecosystems, allowing for bacteria to develop an immunity against the antibiotic. Resistant bacteria cause illnesses, such as salmonella, that are harder to treat with common antibiotics; thus, needing new antibiotics to combat the resistant bacteria. The antibiotics of interest are oxidized penicillin G derivatives that are not commercially available. By using coupling agents, 6-aminopenillic acid forms a peptide bond with aromatic phenols to produce the desired oxidized derivative. Protecting groups were also utilized to protect the carboxylic acids in the compounds. After attempting eight different reactions, an oxidized penicillin G derivative was not successfully synthesized. The reactivity of the carboxylic acids in 6-APA and the aromatic phenols posed a problem that was unable to be overcome.