A Nonenzymic Model for the Coenzyme B12-Dependent Isomerization of Methylmalonyl-SCoA to Succinyl-SCoA

Article abstract of DOI:10.1016/S0040-4020(01)82431-5

Dimethyl bromomethylmalonate (IV) reacts with vitamin B_12s in aqueous solution yielding a relatively unstable carbon-cobalt bonded adduct V, which shows visible spectra in good accord with expectation.The adduct V was allowed to decompose in water, in the dark, at room temperature and at physiological pH.Three products: succinic acid (VI), methylmalonic acid (VIII) and malonic acid (VII) were formed in 3, 18, and 13percent yields respectively.Isolation of the succinic acid rearrangement product provides support for the intermediacy of the carbon-cobalt bond in the coenzyme B₁₂ dependent enzymic carbon-skeleton rearrangement of methylmalonyl-SCoA to succinyl-SCoA.