Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines

Org Biomol Chem. 2006 Jun 7;4(11):2278-84. doi: 10.1039/b604010a. Epub 2006 May 4.

Abstract

An expeditious and highly efficient single-step methodology for the introduction of a phenylalanine moiety into position 8 and 6 of the purine scaffold was developed based on aqueous-phase Pd-catalysed Suzuki-Miyaura cross-coupling reactions of unprotected 4-boronophenylalanine with 8-bromo- or 6-chloropurines. The scope of the methodology was demonstrated by syntheses of unprotected (adenin-8-yl)phenylalanine base, nucleosides, nucleotides and nucleoside triphosphates as well as (purin-6-yl)phenylalanine base and nucleosides. All these products were obtained in high yields and in optically pure form.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes / chemistry*
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemical synthesis
  • Purine Nucleosides / chemistry*
  • Purine Nucleotides / chemistry*
  • Purines / chemical synthesis*
  • Purines / chemistry

Substances

  • Boranes
  • Purine Nucleosides
  • Purine Nucleotides
  • Purines
  • Phenylalanine