2,3-difluorotyrosine at position 356 of ribonucleotide reductase R2: a probe of long-range proton-coupled electron transfer

J Am Chem Soc. 2003 Sep 3;125(35):10506-7. doi: 10.1021/ja036242r.

Abstract

Escherichia coli class I ribonucleotide reductase catalyzes the conversion of ribonucleotides to deoxyribonucleotides and consists of two subunits: R1 and R2. R1 possesses the active site, while R2 harbors the essential diferric-tyrosyl radical (Y*) cofactor. The Y* on R2 is proposed to generate a transient thiyl radical on R1, 35 A distant, through amino acid radical intermediates. To study the putative long-range proton-coupled electron transfer (PCET), R2 (375 residues) was prepared semisynthetically using intein technology. Y356, a putative intermediate in the pathway, was replaced with 2,3-difluorotyrosine (F2Y, pKa = 7.8). pH rate profiles (pH 6.5-9.0) of wild-type and F2Y-R2 were very similar. Thus, a proton can be lost from the putative PCET pathway without affecting nucleotide reduction. The current model involving H* transfer is thus unlikely.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Electrons
  • Escherichia coli / enzymology
  • Hydrogen-Ion Concentration
  • Models, Molecular
  • Molecular Sequence Data
  • Oxidation-Reduction
  • Protons
  • Ribonucleotide Reductases / chemistry*
  • Ribonucleotide Reductases / metabolism*
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemistry*
  • Tyrosine / metabolism*

Substances

  • Protons
  • 3,5-difluorotyrosine
  • Tyrosine
  • Ribonucleotide Reductases
  • ribonucleotide reductase R2 subunit