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四氢蝶呤的¹H-NMR和质谱研究。四氢生物蝶呤生物合成中间体6-丙酮酰四氢蝶呤结构的证据。

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

作者信息

Ghisla S, Kuster T, Steinerstauch P, Leimbacher W, Richter W J, Raschdorf F, Dahinden R, Curtius H C

机构信息

Faculty of Biology, University of Konstanz, Federal Republic of Germany.

出版信息

Eur J Biochem. 1990 Feb 14;187(3):651-6. doi: 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.

摘要

在6-丙酮酰四氢蝶呤合酶存在的情况下,通过1H-NMR光谱对三磷酸二氢新蝶呤的转化进行了跟踪。产物光谱的解释是明确的:它们显示出在不对称C(6)原子上带有立体定向取代基的四氢蝶呤系统的形成。光谱与(3')-CH3官能团的形成以及三磷酸二氢新蝶呤1'和2'氢的完全去除相一致。对同一产物的快原子轰击/质谱研究在m/z 238处产生了一个[M + H]+离子,与6-丙酮酰四氢蝶呤的结构相符。这些数据支持了所提出的6-丙酮酰四氢蝶呤作为四氢生物蝶呤生物合成关键中间体的结构。

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