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Synthesis of the 1-monoester of 2-ketoalkanedioic acids, for example, octyl ?-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 ?-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.

SUBMITTER: Jung ME 

PROVIDER: S-EPMC4099047 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Synthesis of the 1-monoester of 2-ketoalkanedioic acids, for example, octyl α-ketoglutarate.

Jung Michael E ME   Deng Gang G  

The Journal of organic chemistry 20121128 23


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 therapeut  ...[more]

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