Synthesis of enzymatically active D-7,8-dihydroneopterin-3'-triphosphate

Biochem Biophys Res Commun. 1988 May 16;152(3):1193-9. doi: 10.1016/s0006-291x(88)80411-x.

Abstract

The first chemical synthesis of D-neopterin-3'-triphosphate and D-7,8-dihydroneopterin-3'-triphosphate is described. D-neopterin-3'-monophosphate was first 1'-2'-0-formylated with anhydrous formic acid, then activated with 1,1'-carbonyldiimidazole and phosphorylated with n-tributyl-ammonium pyrophosphate. The yield of 3'-NTP was 24%. D-7,8-dihydroneopterin-3'-triphosphate was obtained by chemical (hyposulfite) or catalytic (Pd:H2) reduction of 3'-NTP. Preparations from both reductions were fully active in two different enzymatic systems: synthesis of L-5,6,7,8-tetrahydrobiopterin and in the C-2'-epimerization reaction to L-7,8-dihydromonapterin-3'-triphosphate.

MeSH terms

  • Biopterins / analogs & derivatives
  • Biopterins / chemical synthesis
  • Methods
  • Neopterin*
  • Pteridines / chemical synthesis*

Substances

  • Pteridines
  • dihydroneopterin triphosphate
  • Biopterins
  • neopterin-3'-triphosphate
  • Neopterin
  • sapropterin