A facile and efficient synthesis of (Purin-6-yl)alanines

J Org Chem. 2004 Nov 12;69(23):7985-8. doi: 10.1021/jo048812r.

Abstract

(Purin-6-yl)alanines, a new class of amino acid-nucleobase conjugates, were synthesized by palladium-catalyzed cross-coupling reactions of protected iodozincalanines with 6-iodopurines (9-Bn-6-iodopurine and 9-THP-6-iodopurine as well as acyl-protected 6-iodopurine ribonucleoside and 2-deoxyribonucleoside). Free purine base and nucleosides bearing alanine in position 6 were obtained after complete deprotection of the products of cross-coupling reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis*
  • Alanine / pharmacology
  • Catalysis
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • HeLa Cells
  • Humans
  • Hydrocarbons, Fluorinated / chemistry*
  • Palladium / chemistry*
  • Purine Nucleosides / chemistry
  • Purines / chemical synthesis*
  • Purines / pharmacology

Substances

  • Hydrocarbons, Fluorinated
  • Purine Nucleosides
  • Purines
  • Palladium
  • Alanine