Synthesis of locked cyclohexene and cyclohexane nucleic acids (LCeNA and LCNA) with modified adenosine units

Org Biomol Chem. 2015 Mar 7;13(9):2703-15. doi: 10.1039/c4ob02193b.

Abstract

We describe here the preparation of conformationally locked cyclohexane nucleic acids designed as hybrids between locked nucleic acids (LNAs) and cyclohexene nucleic acids (CeNAs), both of which excel in hybridization with complementary RNAs. We have accomplished the synthesis of these adenine derivatives starting from a simple ketoester and installed all four chiral centres by means of total synthesis. The acquired monomers were incorporated into nonamer oligonucleotides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / chemical synthesis
  • Adenosine / chemistry*
  • Cyclohexanes / chemical synthesis*
  • Cyclohexanes / chemistry
  • Molecular Structure
  • Nucleic Acids / chemical synthesis*
  • Nucleic Acids / chemistry

Substances

  • Cyclohexanes
  • Nucleic Acids
  • Cyclohexane
  • Adenosine