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 μmol/g dry weight of cell. This compound was purified through a high performance liquid chromatography using preparative ∆Pak 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)-β-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.

N-acetylglucosamine, tepidopterin, L-threo-biopterin, Chlorobium tepidum

1H NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)N[C@H]1[C@H](O[C@@H](C)[C@@H](O)c2cnc3[nH]c(N)nc(=O)c3n2)O[C@H](CO)[C@@H](O)[C@@H]1O

440.413 g/mol (C₁₇H₂₄N₆O₈)