Tepidopterin, 1-O-(L-threo-biopterin-2'-yl)-beta-N-acetylglucosamine from Chlorobium tepidum

Biochim Biophys Acta. 1998 Jan 8;1379(1):53-60. doi: 10.1016/s0304-4165(97)00081-0.

Abstract

A novel pterin compound, designated as tepidopterin, was detected from a thermophilic photosynthetic green sulphur bacterium, Chlorobium tepidum. The amount of tepidopterin inside the cell was estimated to be 2-5 micromol g(-1) dry weight of cell. This compound was purified through a high performance liquid chromatography using preparative DeltaPak C18 column. This compound was characterized by chromatographic behavior and by absorption and fluorescence properties. Its structure was determined to be 1-O-(L-threo-biopterin-2'-yl)-beta-N-acetylglucosamine by 1D- and 2D-NMR spectroscopy, mass spectrometry and CD. The relative amount of tetrahydrotepidopterin was estimated to be 96.7% inside the cell, that of dihydrotepidopterin 2.9%, and that of fully oxidized tepidopterin 0.4%. The amount of tepidopterin within the cell increased continuously until the beginning of the stationary phase of the cell growth.

MeSH terms

  • Acetylglucosamine / analogs & derivatives*
  • Acetylglucosaminidase / metabolism
  • Biopterins / analogs & derivatives*
  • Biopterins / chemistry
  • Cell Division / physiology
  • Chlorobi / chemistry*
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Oxidation-Reduction
  • Pterins / analysis*
  • Pterins / chemistry
  • Pterins / isolation & purification
  • Pterins / metabolism
  • Spectrometry, Fluorescence
  • Spectrophotometry

Substances

  • Pterins
  • tepidopterin
  • Biopterins
  • Acetylglucosaminidase
  • Acetylglucosamine