Efficient Preparation of Polyfunctional a-Diketones from Carboxylic Acids

Raymond Conrow, Philip S. Portoghese

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


Many enzymes contain an essential arginyl residue at the active site. Butanedione and other simple α-diketones characteristically inactivate these enzymes by bonding covalently to arginine. In an effort to confer specificity to this interaction, we have sought methods for incorporating an -diketone moiety into polyfunctional inhibitors of such enzymes. The ideal synthetic method for our purpose would involve the conversion of an existing carboxylic acid function into an α-diketone under mild conditions. Here we report on studies directed to developing such a route.

Original languageEnglish (US)
Pages (from-to)938-940
Number of pages3
JournalJournal of Organic Chemistry
Issue number6
StatePublished - Jan 1 1986


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