Open AccessA New Rearrangement Reaction in Tyrosine Metabolism
Author(s) -
FUCHSMETTLER Marianne,
CURTIUS HansChristoph,
BAERLOCHER Kurt,
ETTLINGER Leopold
Publication year - 1980
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1111/j.1432-1033.1980.tb04749.x
Subject(s) - tyrosine , chemistry , lactic acid , metabolism , deuterium , stereochemistry , side chain , biochemistry , medicinal chemistry , organic chemistry , bacteria , biology , genetics , physics , quantum mechanics , polymer
Human faecal specimens were incubated under anaerobic conditions with several dideuterated tyrosine metabolites. 3‐(4‐Hydroxy[3,5‐ 2 H 2 ]phenyl)propionic acid and 3‐(4‐hydroxy[3,5‐ 2 H 2 ]phenyl)lactic acid yielded the rearrangement product 3‐(3‐hydroxy[2,4‐ 2 H 2 ]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.