Efficient synthesis of azide-bearing cofactor mimics

J Org Chem. 2004 Feb 20;69(4):1425-8. doi: 10.1021/jo035485z.

Abstract

8-Azido-5'-aziridino-5'-deoxyadenosine (6), a novel cofactor mimic, was synthesized in nine steps from commercially available 2',3'-isopropylideneadenosine in approximately 4% overall yield. Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation of the 5' amino group with iodoethanol necessitated by the high degree of lability endowed by the aryl azide moiety. Aziridine 6 is envisioned as a useful biochemical tool by which to probe DNA and protein methylation patterns.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis*
  • Adenosine / chemistry*
  • Azides / chemical synthesis*
  • Azides / chemistry
  • Aziridines / chemical synthesis*
  • Aziridines / chemistry
  • Molecular Probes / chemical synthesis*
  • Molecular Probes / chemistry

Substances

  • 8-azido-5'-aziridino-5'-deoxyadenosine
  • Azides
  • Aziridines
  • Molecular Probes
  • 2',3'-isopropylideneadenosine
  • Adenosine