Syntheses of 5-formyl- and 5-carboxyl-dC containing DNA oligos as potential oxidation products of 5-hydroxymethylcytosine in DNA

Org Lett. 2011 Jul 1;13(13):3446-9. doi: 10.1021/ol201189n. Epub 2011 Jun 7.

Abstract

To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH(4) produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.

Publication types

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

MeSH terms

  • 5-Methylcytosine / analogs & derivatives
  • Cytosine / analogs & derivatives*
  • Cytosine / chemistry
  • DNA / chemical synthesis*
  • DNA / chemistry
  • Deoxycytidine / analogs & derivatives*
  • Deoxycytidine / chemistry
  • Methylation
  • Molecular Structure
  • Oligonucleotides / chemical synthesis*
  • Oxidation-Reduction

Substances

  • Oligonucleotides
  • Deoxycytidine
  • 5-hydroxymethylcytosine
  • 5-Methylcytosine
  • Cytosine
  • DNA