New RNA purine building blocks, 4'-selenopurine nucleosides: first synthesis and unusual mixture of sugar puckerings

Chemistry. 2013 Apr 26;19(18):5528-32. doi: 10.1002/chem.201300741. Epub 2013 Mar 28.

Abstract

Writer's blocks: The first synthesis of RNA purine building blocks, 4'-selenoadenosine and 4'-selenoguanosine was achieved from D-ribose by regioisomeric rearrangement, which was confirmed by X-ray crystallography. 4'-Selenoadenosine exists in an unusual mixture of north and south conformers in the solid state.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / chemistry
  • Crystallography, X-Ray
  • Guanosine / analogs & derivatives*
  • Guanosine / chemical synthesis
  • Guanosine / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Purines / chemical synthesis*
  • Purines / chemistry
  • RNA / chemistry*
  • Ribose / chemistry*
  • Stereoisomerism

Substances

  • 4'-selenoadenosine
  • 4'-selenoguanosine
  • Nucleosides
  • Organoselenium Compounds
  • Purines
  • Guanosine
  • RNA
  • Ribose
  • Adenosine