2'-deoxy-1-methylpseudocytidine, a stable analog of 2'-deoxy-5-methylisocytidine

Bioorg Med Chem. 2009 May 15;17(10):3728-32. doi: 10.1016/j.bmc.2009.03.047. Epub 2009 Mar 27.

Abstract

2'-deoxy-5-methylisocytidine is widely used in assays to personalize the care of patients infected with HIV, hepatitis C, and other infectious agents. However, oligonucleotides that incorporate 2'-deoxy-5-methylisocytidine are expensive, because of its intrinsic chemical instability. We report here a C-glycoside analog that is more stable and, in oligonucleotides, pairs with 2'-deoxyisoguanosine, contributing to duplex stability about as much as a standard 2'-deoxycytidine and 2'-deoxyguanosine pair.

Publication types

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

MeSH terms

  • Base Pairing
  • Base Sequence
  • Chromatography, High Pressure Liquid
  • Cytidine / analogs & derivatives*
  • Cytidine / chemical synthesis
  • Cytidine / chemistry
  • Oligodeoxyribonucleotides / chemical synthesis
  • Oligodeoxyribonucleotides / chemistry
  • Transition Temperature

Substances

  • 2'-deoxy-1-methylpseudocytidine
  • 2'-deoxy-5-methylisocytidine
  • Oligodeoxyribonucleotides
  • Cytidine