Abstract

This chapter discusses the preparation, analysis, and biochemical applications of chiral methyl groups. The most common approach by far involves conversion of the chiral methyl group into the methyl group of acetic acid by a series of stereospecific reactions of known steric course. The chiral acetic acid is mixed with a small amount of [14C]acetic acid and is converted into the coenzyme A ester either enzymically by incubation with acetate kinase and phosphate acetyltransferase, or chemically by the anhydride method. An important task in many biochemical studies involving chiral methyl groups is the excision of the methyl group from the environment in which it has been generated and its conversion into acetate for chirality analysis, using a stereochemically defined reaction sequence that does not jeopardize the chiral integrity of the methyl group. In the case of carbon-bound methyl groups, the Kuhn-Roth oxidation or milder versions of it usually serve for this purpose.

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