Journal of the Chemical Society. Perkin transactions I p. 1355 - 1362 (1985)
Update date:2022-08-29
Topics:
Gani, David
Young, Douglas W.
A mammalian enzyme system has been used to study the stereochemistry of the catabolism of the pyrimidine uracil (1) to the amino acid β-alanine (4).Use of <5-(2)H>- and <6-(2)H>- uracils and of (2)H2O in the incubations yielded sterospecifically deuteriated samples of β-alanine.Assays, involving total synthesis of samples of β-alanine unambigously labelled with deuterium in each of the four C-H bonds have shown that, in the first step in the catabolic process, uracil is reduced by dihydrouracil dehydrogenase with overall anti addition of hydrogen, at the si face at C-6 and the si face at C-5.
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