1H‐NMR and mass spectrometric studies of tetrahydropterins
Open Access
- 1 February 1990
- journal article
- research article
- Published by Wiley in European Journal of Biochemistry
- Vol. 187 (3) , 651-656
- https://doi.org/10.1111/j.1432-1033.1990.tb15349.x
Abstract
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.This publication has 35 references indexed in Scilit:
- Biosynthesis of biopterin studies on the mechanism of 6-pyruvoyltetrahydropteridine synthaseBiochemical and Biophysical Research Communications, 1988
- Biosynthesis of tetrahydrobiopterin: Conversion of dihydroneopterin triphosphate to tetrahydropterin intermediatesBiochemical and Biophysical Research Communications, 1985
- Purification and properties of the phosphate eliminating enzyme involved in the biosynthesis of BH4 in manBiochemical and Biophysical Research Communications, 1985
- Two new tetrahydropterin intermediates in the adrenal medullary de novo biosynthesis of tetrahydrobiopterinBiochemical and Biophysical Research Communications, 1984
- Intermediates in the enzymic synthesis of tetrahydrobiopterin in DrosophilamelanogasterBiochemical and Biophysical Research Communications, 1984
- Tetrahydro-sepiapterin is an intermediate in tetrahydrobiopterin biosynthesisBiochemical and Biophysical Research Communications, 1983
- Über Pterinchemie. 72. Mitteilung. Trennung der Diastereomeren (6R)‐ und (6S)‐5,6,7,8‐Tetrahydro‐L‐biopterinHelvetica Chimica Acta, 1979
- Über Pterinchemie. 65 Mitteilung [1]. Herstellung von (6 R, S)‐5,6,7,8‐Tetrahydro‐L‐biopterin, 7,8‐Dihydro‐L‐biopterin, L‐Sepiapterin, Deoxysepiapterin, (6 R, S)‐5,6‐Dihydrodeoxysepiapterin und 2′‐DeoxybiopterinHelvetica Chimica Acta, 1978
- Chemistry of dihydropterins and tetrahydropterinsJournal of Inherited Metabolic Disease, 1978
- Über Pterinchemie. 32. Mitteilung [1]. Synthese des natürlichen D‐Neopterins und L‐MonapterinsHelvetica Chimica Acta, 1970