A New Rearrangement Reaction in Tyrosine Metabolism

Abstract
Human fecal specimens were incubated under anaerobic conditions with several dideuterated tyrosine metabolites. 3-(4-Hydroxy[3,5-2H2]phenyl)propionic acid and 3-(4-hydroxy[3,5-2H2]phenyl)lactic acid yielded the rearrangement product 3-(3-hydroxy[2,4-2H2]phenyl)propionic acid. The starting materials and the product all contained 2 D atoms both ortho to the hydroxyl group. The rearrangement reaction must depend on a shift of the side-chain.