Synthesis and thermal stabilities of oligonucleotides containing 2'-O,4'-C-methylene bridged nucleic acid with a phenoxazine base

Org Biomol Chem. 2017 Oct 4;15(38):8145-8152. doi: 10.1039/c7ob01874f.

Abstract

We designed and synthesized a novel artificial 2'-O,4'-C-methylene bridged nucleic acid (2',4'-BNA/LNA) with a phenoxazine nucleobase and named this compound BNAP. Oligodeoxynucleotide (ODN) containing BNAP showed higher binding affinities toward complementary DNA and RNA as compared to ODNs bearing 2',4'-BNA/LNA with 5-methylcytosine or 2'-deoxyribonucleoside with phenoxazine. Thermodynamic analysis revealed that BNAP exhibits properties associated with the phenoxazine moiety in DNA/DNA duplexes and characteristics associated with the 2',4'-BNA/LNA moiety in DNA/RNA duplexes.

MeSH terms

  • DNA / chemistry
  • Nucleic Acid Conformation
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry
  • Oxazines / chemistry*
  • Thermodynamics

Substances

  • Oligonucleotides
  • Oxazines
  • DNA
  • phenoxazine