6-pyruvoyl-5,6,7,8-tetrahydropterin
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Surname | 6-pyruvoyl-5,6,7,8-tetrahydropterin | |||||||||
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Molecular formula | C 9 H 11 N 5 O 3 | |||||||||
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Molar mass | 237.22 g mol −1 | |||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
6-Pyruvoyl-tetrahydropterin is a heterocyclic compound which belongs to the natural product class of pterins , in a broader sense pteridines .
The name of the molecule is derived from the C 3 side chain at C-6 of the pterin heterocycle. She wears two adjacent carbonyl groups and structurally corresponds to a pyruvic acid residue ( Pyruvic acid ). The substituent (CH 3 COCO−) is therefore referred to as the pyruvoyl residue.
history
In investigations into the biosynthesis of 5,6,7,8-tetrahydrobiopterin (BH4, sapropterin ) from dihydroneopterin triphosphate , which in turn is formed over several stages from guanosine triphosphate (GTP), it became probable that an unstable intermediate product could occur as a precursor, which the structure of 6-pyruvoyl-5,6,7,8-tetrahydropterin (PPH4) was assigned.
Isolation of the labile molecule PPH4 proved difficult. At least 1 H-NMR spectroscopy and the mass spectrum provided reasonable evidence for its existence.
biochemistry
The conversion of dihydroneopterin triphosphate to PPH4 is catalyzed by the enzyme 6-pyruvoyl-H4-pterin synthase (PTPS, PPH4S, EC 4.6.1.10 ). The carbonyl groups of the side chain are then hydrogenated to the diol (BH4), with the coenzyme NADPH acting as a hydrogen source, in cooperation with the enzyme sepiapterin reductase . The intermediate stage 6-lactoyl-5,6,7,8-tetrahydrosepiapterin may also be formed first.
Web links
Individual evidence
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ H.-Ch. Curtius, D. Heintel, S. Ghisla, T. Kuster, W. Leimbacher, A. Niederwieser, EUR. J. Biochem. 148: 413 (1985).
- ↑ S. Gisla, Shin-Ichiro Takikawa, P. Steinerstauch, T. Hasler, H.-Ch. Curtius, in Chemistry and Biology of Pteridines, Edit. BA Cooper, pp. 299-303, de Gruyter, Berlin, 1986
- ^ WJ Richter, F. Raschdorf, R. Dahinden, A. Niederwieser, H.-Ch. Curtius, W. Leimbacher, Th. Kuster, in Unconjugated Pterins and Related Biogenic Amines, H.-Ch. Curtius, N. Blau, Eds., De Gruyter, Berlin 1987.