6-pyruvoyl-5,6,7,8-tetrahydropterin

Structural formula
General
Surname	6-pyruvoyl-5,6,7,8-tetrahydropterin
other names	Dyspropter; 1- (2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl) propane-1,2-dione ( IUPAC );
Molecular formula	C 9 H 11 N 5 O 3
External identifiers / databases
PubChem	128973
Wikidata	Q245508
properties
Molar mass	237.22 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	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

Wikibooks: Biochemistry and Pathobiochemistry: Biopterin Metabolism - Learning and Teaching Materials

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.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] H.-Ch. Curtius, D. Heintel, S. Ghisla, T. Kuster, W. Leimbacher, A. Niederwieser, EUR. J. Biochem. 148: 413 (1985).

[3] 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

[4] 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.