There is a wide need for the discovery and development of new antimicrobial agents due to the evolution of microbial resistance to commonly applied antibiotics, particularly of life-threatening pathogens. Fatty acids are known for having an interesting activity against viruses and bacteria. They can prevent growth or even cause the direct death of the microorganisms. Besides this potential, fatty acids exert harmful effects on pathogens by interfering with virulence mechanisms, such as preventing biofilm formation and inhibiting the production of toxins and enzymes. These multiple modes of action against microbes make fatty acids a prominent class of substances with antimicrobial activity.<br/>In this study, we have identified a great number of fatty acids present in domestic cat urine samples. GC-MS analysis of the extracts has shown the presence of two unusual ethyl branched fatty acids. Based on the mass fragmentation pattern, the structures proposal are 4,12-diethyltetradecanoic and 4,14-diethylhexadecanoic acid. To prove the identity of the compounds a synthetic route was developed. As shown in the Scheme below, the strategy is to combine building blocks in a convergent synthesis, coupling these blocks through a Fouquet-Schlosser approach of the Grignard reaction. The ethyl branches will rise from the commercially available materials 4-ethylcyclohexanone and 2-ethyl-1-bromobutane. The central building block will differ for the synthesis of the different structures of the two fatty acids, which will be 1-bromohexan-6-ol or 1-bromobutan-4-ol, determining the length of the main chain. After the synthesis, bioassays will be performed to observe if the compounds have activity against antibiotic-resistant strains of virus and bacteria. The structures will be tested alone and in combination with common antibiotics, to test whether they can also have a synergistic action.

Unusual ethyl branched chain fatty acids: Synthesis and biological evaluation

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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