Product deuterium isotope effects for orotidine 5'-monophosphate decarboxylase: effect of changing substrate and enzyme structure on the partitioning of the vinyl carbanion reaction intermediate

J Am Chem Soc. 2010 May 26;132(20):7018-24. doi: 10.1021/ja102408k.

Abstract

A product deuterium isotope effect (PIE) of 1.0 was determined as the ratio of the yields of [6-(1)H]-uridine 5'-monophosphate (50%) and [6-(2)H]-uridine 5'-monophosphate (50%) from the decarboxylation of orotidine 5'-monophosphate (OMP) in 50/50 (v/v) HOH/DOD catalyzed by orotidine 5'-monophosphate decarboxylase (OMPDC) from Saccharomyces cerevisiae, Methanothermobacter thermautotrophicus, and Escherichia coli. This unitary PIE eliminates a proposed mechanism for enzyme-catalyzed decarboxylation in which proton transfer from Lys-93 to C-6 of OMP provides electrophilic push to the loss of CO(2) in a concerted reaction. We propose that the complete lack of selectivity for the reaction of solvent H and D, which is implied by the value of PIE = 1.0, is enforced by restricted C-N bond rotation of the -CH(2)-NL(3)(+) group of the side chain of Lys-93. A smaller PIE of 0.93 was determined as the ratio of the product yields for OMPDC-catalyzed decarboxylation of 5-fluoroorotidine 5'-monophosphate (5-FOMP) in 50/50 (v/v) HOH/DOD. Mutations on the following important active-site residues of OMPDC from S. cerevisiae have no effect on the PIE on OMPDC-catalyzed decarboxylation of OMP or decarboxylation of 5-FOMP: R235A, Y217A, Q215A, S124A, and S154A/Q215A.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Biocatalysis
  • Deuterium*
  • Escherichia coli / enzymology
  • Methanobacteriaceae / enzymology
  • Mutation
  • Nuclear Magnetic Resonance, Biomolecular
  • Orotidine-5'-Phosphate Decarboxylase / chemistry*
  • Orotidine-5'-Phosphate Decarboxylase / genetics
  • Orotidine-5'-Phosphate Decarboxylase / metabolism*
  • Ribonucleotides / metabolism
  • Saccharomyces cerevisiae / enzymology
  • Uridine Monophosphate / analogs & derivatives
  • Uridine Monophosphate / metabolism

Substances

  • 5-fluoroorotidine 5'-phosphate
  • Ribonucleotides
  • orotidylic acid
  • Deuterium
  • Uridine Monophosphate
  • Orotidine-5'-Phosphate Decarboxylase