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

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1990

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Kuster, Thomas
Steinerstauch, Petra
Leimbacher, Walter
Richter, Wilhelm Johannes
Raschdorf, Fritz
Dahinden, Roland
Curtius, Hans-Christoph

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European Journal of Biochemistry. 1990, 187(3), pp. 651-656. ISSN 0014-2956. eISSN 1432-1033. Available under: doi: 10.1111/j.1432-1033.1990.tb15349.x

Zusammenfassung

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.

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570 Biowissenschaften, Biologie

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ISO 690GHISLA, Sandro, Thomas KUSTER, Petra STEINERSTAUCH, Walter LEIMBACHER, Wilhelm Johannes RICHTER, Fritz RASCHDORF, Roland DAHINDEN, Hans-Christoph CURTIUS, 1990. 1H-NMR and mass spectrometric studies of tetrahydropterins : evidence for the structure of 6-pyruvoyl tetrahydropterin, an intermediate in the biosynthesis of tetrahydrobiopterin. In: European Journal of Biochemistry. 1990, 187(3), pp. 651-656. ISSN 0014-2956. eISSN 1432-1033. Available under: doi: 10.1111/j.1432-1033.1990.tb15349.x
BibTex
@article{Ghisla19901HNMR-6578,
  year={1990},
  doi={10.1111/j.1432-1033.1990.tb15349.x},
  title={1H-NMR and mass spectrometric studies of tetrahydropterins : evidence for the structure of 6-pyruvoyl tetrahydropterin, an intermediate in the biosynthesis of tetrahydrobiopterin},
  number={3},
  volume={187},
  issn={0014-2956},
  journal={European Journal of Biochemistry},
  pages={651--656},
  author={Ghisla, Sandro and Kuster, Thomas and Steinerstauch, Petra and Leimbacher, Walter and Richter, Wilhelm Johannes and Raschdorf, Fritz and Dahinden, Roland and Curtius, Hans-Christoph}
}
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