Methyltransferase-directed derivatization of 5-hydroxymethylcytosine in DNA

Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2090-3. doi: 10.1002/anie.201007169. Epub 2011 Jan 26.

Abstract

Cytosine modification by AdoMet–dependent DNA methyltransferases is part of an epigenetic regulatory network in vertebrates. Here we show that, in the absence of AdoMet, bacterial cytosine-5 methyltransferases can catalyze condensation of aliphatic thiols and selenols to 5-hydroxymethylcytosine in DNA yielding 5-chalcogenomethyl derivatives. These new atypical reactions open new ways for sequence-specific derivatization and analysis of 5-hydroxymethylcytosine, a recently discovered nucleobase in mammalian DNA

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 5-Methylcytosine / analogs & derivatives
  • Cytosine / analogs & derivatives*
  • Cytosine / chemistry
  • Cytosine / metabolism
  • DNA (Cytosine-5-)-Methyltransferases / metabolism*
  • DNA / chemistry
  • DNA / metabolism*
  • DNA Methylation
  • S-Adenosylmethionine / metabolism
  • Selenium Compounds / chemistry
  • Selenium Compounds / metabolism
  • Sulfhydryl Compounds / chemistry

Substances

  • Selenium Compounds
  • Sulfhydryl Compounds
  • selenol
  • 5-hydroxymethylcytosine
  • 5-Methylcytosine
  • S-Adenosylmethionine
  • Cytosine
  • DNA
  • DNA (Cytosine-5-)-Methyltransferases