Sepiapterin

• 6 - ( S)- lactoyl -7 ,8- dihydropterin
• 2-amino- 7 ,8 -dihydro -6 -[( S)-2 -hydroxy-1 - oxopropyl ] -4 (1H)- pteridinone

Yellow crystalline powder, drusen -like crystals

Fixed

Soluble in water, insoluble in acetone and most of the organic solvents

Template: Infobox chemical / molecular formula search available

Sepiapterin is a chiral heterocyclic substance from the class of pterins and pteridines.

Discovery

In the eyes of the fruit fly Drosophila yellow and red pigments are found to fluoresce in part. A yellow pigment was discovered in Drosophila melanogaster (wild type), in increased concentration in the mutant sepia and in the 1950s by Forrest and Mitchell at the California Institute of Technology ( Pasadena ) was isolated as yellow crystals. Viscontini and Möhlmann found next to Sepiapterin an isomer, which Isosepiapterin was called. The structural formula of Sepiapterins was only 1978/1979 by Max Viscontini and employees ( Zurich ), and Wolfgang Pfleiderer (Konstanz ) are determined. It is a 7.8 - dihydropterin, which is related to the biopterin, but in position 6 carries a C3 chain with a carbonyl group. The side chain has the structure of lactic acid ( lactoyl residue ), and has the (S ) configuration.

Further populations

The compound was also in the epidermis of the silkworm ( Bombyx mori mutant lem ) and found in the skin of amphibians and fish. The occurrence of trace amounts in the urine of mammals and humans indicates that sepiapterin is an intermediate ( intermediate) in the metabolism of many organisms.

Biochemistry

An enzymatic synthesis of sepiapterin from D -erythro- dihydroneopterin triphosphate by extracts from the kidneys of chicks has been described.

The enzyme sepiapterin reductase catalyzes the hydrogenation of the carbonyl group at C- 1 ' by NADPH, which dihydrobiopterin is formed. To conclude this to tetrahydrobiopterin ( BH4) is reduced.

Enzymatic formation of sepiapterin from D -erythro- dihydroneopterin triphosphate and hydrogenation to dihydrobiopterin.