Facile synthesis of hydroxymethylcytosine-containing oligonucleotides and their reactivity upon osmium oxidation

Org Biomol Chem. 2011 Jun 7;9(11):4176-81. doi: 10.1039/c1ob05247k. Epub 2011 Apr 15.

Abstract

DNA strands containing a 5-hydroxymethylcytosine ((hm)C), which have recently been found in neuron cells and embryonic stem cells, were synthesized through a facile synthetic technique. The (hm)C-containing strands were efficiently oxidized at (hm)C using an osmium oxidation assay. The (hm)C was oxidized as easily as 5-methylcytosine, which can be distinguished from unmethylated cytosine.

MeSH terms

  • 5-Methylcytosine / analogs & derivatives
  • Crystallography, X-Ray
  • Cytosine / analogs & derivatives*
  • Cytosine / chemistry
  • Models, Molecular
  • Molecular Structure
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry
  • Osmium / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism
  • Transition Temperature

Substances

  • Oligonucleotides
  • 5-hydroxymethylcytosine
  • Osmium
  • 5-Methylcytosine
  • Cytosine