title: Synthesis of the 1-monoester of 2-ketoalkanedioic acids, for example, octyl α-ketoglutarate.
abstract: Oxidative cleavage of cycloalkene-1-carboxylates, made from the corresponding carboxylic acids, and subsequent oxidation of the resulting ketoaldehyde afforded the important 1-monoesters of 2-ketoalkanedioic acids. Thus ozonolysis of octyl cyclobutene-1-carboxylate followed by sodium chlorite oxidation afforded the 1-monooctyl 2-ketoglutarate. This is a cell-permeable prodrug form of α-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Gang
authors.initials: G
authors.lastname: Deng
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D003516:Cycloparaffins / Q000737:chemistry*; D004952:Esters; D007656:Ketoglutaric Acids / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D002264:Carboxylic Acids; D003516:Cycloparaffins; D004952:Esters; D007656:Ketoglutaric Acids