A practical route to 3'-amino-3'-deoxyadenosine derivatives and puromycin analogues

J Org Chem. 2003 Mar 7;68(5):2038-41. doi: 10.1021/jo026627c.

Abstract

3'-aminoacylamino-3'-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized from adenosine. They key 3'-azido derivative 10 was obtained through a 3'-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was developed for the oxidation step using the Garegg reagent. The coupling reaction between an Fmoc-l-amino acid and the fully protected form of 3'-amino-3'-deoxyadenosine 11 furnished the aminoacylated compounds 12 in high yields. The puromycin analogues were obtained in 10 steps and up to 23% (14c) overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine
  • Chemistry, Organic / methods
  • Deoxyadenosines / analysis
  • Deoxyadenosines / chemical synthesis*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Puromycin / analogs & derivatives*
  • Puromycin / analysis
  • Puromycin / chemical synthesis*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Deoxyadenosines
  • Indicators and Reagents
  • 3'-amino-3'-deoxyadenosine
  • Puromycin
  • Adenosine