Diastereomers of neopterin and biopterin in human urine

Biol Chem Hoppe Seyler. 1992 Oct;373(10):1061-5. doi: 10.1515/bchm3.1992.373.2.1061.

Abstract

A new pteridine compound, named umanopterin, was isolated from human urine both of cancer patients and non-cancer controls. The structure was confirmed to be 2-amino-4(3H)-oxo-6-[(1'R,2'R)-1',2',3'-trihydroxypropyl]pteridine , a diastereomer of neopterin. The amount of umanopterin relative to neopterin was about 10%, which was practically the same among the non-cancer controls and the patients of various cancers. A small amount of a threo diastereomer of biopterin, named orinapterin, was isolated from human urine for the first time. Its structure was shown to be 2-amino-4(3H)-oxo-6-[(1'S,2'S)-1',2'-dihydroxypropyl]pteridine. A non-enzymatic transformation of 7,8-dihydroneopterin and 7,8-dihydrobiopterin by a mechanism analogous to keto-enol tautomerism is postulated for the formation of umanopterin and orinapterin in human body.

MeSH terms

  • Acetylation
  • Biopterins / analogs & derivatives*
  • Biopterins / chemistry
  • Biopterins / urine*
  • Carcinoma, Hepatocellular / urine
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Female
  • Humans
  • Liver Neoplasms / urine
  • Magnetic Resonance Spectroscopy
  • Male
  • Neoplasms / urine*
  • Neopterin
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism

Substances

  • Biopterins
  • Neopterin