Synthesis of phosphoramidate prodrugs: ProTide approach

Curr Protoc Nucleic Acid Chem. 2013 Jun:Chapter 15:15.5.1-15.5.15. doi: 10.1002/0471142700.nc1505s53.

Abstract

The ProTide (pronucleotide) approach is a prodrug strategy elaborated to deliver nucleoside monophosphate into the cell, circumventing the first and inefficient rate-limiting phosphorylation step of nucleosides and improving the cellular penetration of nucleotides. The ProTide of a nucleoside phosphate is a phosphoramidate prodrug consisting of an amino acid ester promoiety linked via P-N bond to a nucleoside aryl phosphate. Such prodrugs have increased lipophilicity and thus are capable of altering cell and tissue distribution. The ProTide technology was successfully and extensively applied to a wide variety of nucleoside phosphates, endowed with antiviral and anticancer activity. This unit describes two different synthetic strategies allowing the preparation of phosphoramidates of 6-O-methyl-2'-β-C-methylguanosine as model compounds for nucleosides having only the 5'-OH as reactive hydroxyl group, and phosphoramidates of 2'-β-D-arabinouridine (AraU) as model compounds for nucleosides containing two or more reactive hydroxyl groups.

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / pharmacology*
  • Esters / chemistry
  • Guanosine / analogs & derivatives*
  • Guanosine / chemistry
  • Guanosine / pharmacology
  • Hepacivirus / drug effects
  • Nucleosides / chemistry
  • Nucleosides / metabolism*
  • Nucleotides / chemistry
  • Nucleotides / metabolism*
  • Phosphorylation
  • Prodrugs / chemical synthesis*
  • Prodrugs / metabolism

Substances

  • Antiviral Agents
  • Esters
  • Nucleosides
  • Nucleotides
  • Prodrugs
  • Guanosine
  • 6'-O-methylguanosine