[47] Chloromethyl ketone derivatives of fatty acids

Add time:07/17/2019    Source:sciencedirect.com

Publisher SummaryThis chapter discusses various aspects of chloromethyl ketone derivatives of fatty acids. α-Haloketones are very susceptible to nucleophilic attack, which makes this functional group ideally suited for the design of specific enzyme active-site-directed inhibitors. Classic examples of this use are found in the synthesis of α-N-tosylphenylethylchloromethyl ketone and α-N-tosyllysylchloromethyl ketone as specific inhibitors for proteolytic enzymes. The class I chloromethylketone analogs represent one of the simplest type of analogs of fatty acids containing the reactive halomethyl-ketone functional group. They suffer from the drawback that, chemical manipulation has removed the carboxyl group and these results in a profound solubility change in that class I analogs are virtually insoluble in water. Radioactive inhibitors for binding studies can be conveniently synthesized by acid-catalyzed proton exchange from the methylene groups adjacent to the carbonyl. Potential applications for the chloromethyl ketone fatty acid analogs may be found in all areas of enzymology, involving the binding and metabolism of fatty acids.

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