Synthesis and characterization of a DNA analogue stabilized by mercapto C-nucleoside induced disulfide bonding

Bioorg Med Chem Lett. 2004 May 17;14(10):2459-62. doi: 10.1016/j.bmcl.2004.03.015.

Abstract

A redox-active nucleobase analogue of a nucleotide was synthesized and incorporated into DNA using phosphoramidite chemistry. An analogue-containing oligonucleotide in the absence of a reducing reagent formed a stable duplex with a substantially higher melting temperature compared to that of a standard DNA duplex of the same length.

MeSH terms

  • Base Sequence
  • DNA / chemical synthesis*
  • DNA / chemistry
  • Disulfides / chemistry*
  • Nucleic Acid Conformation
  • Phase Transition
  • Sulfhydryl Compounds
  • Temperature
  • Thionucleotides / chemical synthesis*

Substances

  • Disulfides
  • Sulfhydryl Compounds
  • Thionucleotides
  • DNA