Catalysis by desolvation: the catalytic prowess of SAM-dependent halide-alkylating enzymes

J Am Chem Soc. 2013 Oct 2;135(39):14473-5. doi: 10.1021/ja406381b. Epub 2013 Sep 18.

Abstract

In the biological fixation of halide ions, several enzymes have been found to catalyze alkyl transfer from S-adenosylmethionine to halide ions. It proves possible to measure the rates of reaction of the trimethylsulfonium ion with I(-), Br(-), Cl(-), F(-), HO(-), and H2O in water at elevated temperatures. Comparison of the resulting second-order rate constants, extrapolated to 25 °C, with the values of k(cat)/K(m) reported for fluorinase and chlorinase indicates that these enzymes enhance the rates of alkyl halide formation by factors of 2 × 10(15)- and 1 × 10(17)-fold, respectively. These rate enhancements, achieved without the assistance of cofactors, metal ions, or general acid-base catalysis, are the largest that have been reported for an enzyme that acts on two substrates.

Publication types

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

MeSH terms

  • Alkylation
  • Anions / chemistry
  • Anions / metabolism
  • Bacterial Proteins / metabolism*
  • Halogens / chemistry
  • Halogens / metabolism*
  • Micromonosporaceae / enzymology*
  • Oxidoreductases / metabolism*
  • S-Adenosylmethionine / metabolism*
  • Streptomyces / enzymology*
  • Water / chemistry
  • Water / metabolism

Substances

  • Anions
  • Bacterial Proteins
  • Halogens
  • Water
  • S-Adenosylmethionine
  • Oxidoreductases
  • fluorinase