Synthesis of an enantiomeric DNA oligomer and its T-HgII-T base-pair formation

Nucleic Acids Symp Ser (Oxf). 2007:(51):187-8. doi: 10.1093/nass/nrm094.

Abstract

Unnatural "L-DNA" containing 2'-deoxy-L-ribose backbone instead of natural 2'-deoxy-D-ribose was synthesized and evaluated by (1)H NMR, CD spectra. Proton ((1)H) NMR spectra of natural DNA (D-TpT) and L-DNA (L-TpT) are fully consistent with each other. In CD spectra, however, spectrum of L-TpT was reversed, relative to that of D-TpT. These results indicate that L-TpT is an isomer with a mirror image configuration of D-TpT. In summary, we have synthesized enantiomeric L-DNA, and the L-DNA would be materials for nanodevices and tools for exploring why the D-isomer of DNA molecules was selected as a bio-molecule.

MeSH terms

  • Base Pairing
  • DNA / chemistry*
  • Mercury / chemistry
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Oligodeoxyribonucleotides / chemistry
  • Stereoisomerism
  • Thymine / chemistry

Substances

  • Oligodeoxyribonucleotides
  • DNA
  • Mercury
  • Thymine