title: A new rearrangement reaction in tyrosine metabolism.
abstract: Human faecal 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 rearrangment product 3-(3-hydroxy[2,4-2H2]phenyl)propionic acid. The starting materials as well as the product all contained two deuterium atoms both ortho to the hydroxyl group. Therefore the rearrangement reaction must depend on a shift of the side chain.
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D003903:Deuterium; D005243:Feces; D006801:Humans; D013058:Mass Spectrometry; D010661:Phenylketonurias / Q000378:metabolism*; D010666:Phenylpropionates / Q000378:metabolism; D014443:Tyrosine / Q000378:metabolism*
chemical_list: D010666:Phenylpropionates; C001418:4-hydroxyphenyllactic acid; D014443:Tyrosine; C008869:phloretic acid; D003903:Deuterium