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Abstract
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 13% yields respectively. Isolation of the succinic acid rearrangement product provides support for the intermediacy of the carbon-cobalt bond in the coenzyme B 12 dependent enzymic carbon-skeleton rearrangement of methylmalonyl-SCoA to succinyl-SCoA.
Published Version
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