1H-NMR and mass spectrometric studies of tetrahydropterins. Evidence for the structure of 6-pyruvoyl tetrahydropterin, an intermediate in the biosynthesis of tetrahydrobiopterin

Eur J Biochem. 1990 Feb 14;187(3):651-6. doi: 10.1111/j.1432-1033.1990.tb15349.x.

Abstract

The conversion of dihydroneopterin triphosphate in the presence of 6-pyruvoyl tetrahydropterin synthase was followed by 1H-NMR spectroscopy. The interpretation of the spectra of the product is unequivocal: they show formation of a tetrahydropterin system carrying a stereospecifically oriented substituent at the asymmetric C(6) atom. The spectra are compatible with formation of a (3')-CH3 function, and with complete removal of the 1' and 2' hydrogens of dihydroneopterin triphosphate. The fast-atom-bombardment/mass spectrometry study of the same product yields a [M + H]+ ion at m/z 238 compatible with the structure of 6-pyruvoyl tetrahydropterin. The data support the proposed structure of 6-pyruvoyl tetrahydropterin as a key intermediate in the biosynthesis of tetrahydrobiopterin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohol Oxidoreductases / metabolism
  • Biopterins / analogs & derivatives*
  • Biopterins / biosynthesis
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Chemical
  • Neopterin / analogs & derivatives
  • Oxidation-Reduction
  • Phosphorus-Oxygen Lyases*
  • Pteridines / metabolism
  • Pterins* / analysis
  • Stereoisomerism

Substances

  • Pteridines
  • Pterins
  • tetrahydropterin
  • dihydroneopterin triphosphate
  • Biopterins
  • Neopterin
  • dyspropterin
  • Alcohol Oxidoreductases
  • Phosphorus-Oxygen Lyases
  • 6-pyruvoyltetrahydropterin synthase
  • sapropterin