72(P-61) 微生物中の微量テトラヒドロプテリンの絶対構造の決定(ポスター発表の部)

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(6R)-5,6,7,8-Tetrahydrobiopterin(1) is the cofactor for biosyntheses of catecholamines and NO in mammals. Tetrahymena pyriformis has D-monapterin (2) as a major pterin, and Escherichia coil has the L-isomer (3). In those microorganisms, tetrahydromonapterin (4 and 5) may play important biological roles described above. We here present the determination of absolute configuration of tetrahydromonapterin (4 and 5) in those microorganisms. The cell extracts were oxidized with iodine under acidic or alkaline conditions followed by HPLC analysis. The major peak was identical with synthetic monapterin (2 or 3). Moreover, peak areas under acidic conditions were larger than those under alkaline oxidations, 1.6 times in extracts of T. pyriformis and 4.8 times in extracts of E. coli, respectively. So it is confirmed that monapterins in those microorganisms exit as tetrahydro-forms (4 and 5). In order to determine absolute configurations of side chains of tetrahydromonapterins (4 and 5), FDCD spectra were measured. In comparison with synthetic standards, major fluorescent peaks were identified as D-monapterin (2) in T. Pyriformis, and as L-monapterin (3) in E. coli, respectively The absolute configuration at 6-position of tetrahydro-D-monapterin (2) in T. Pyriformis, the extracts were acetylated and then analyzed by LC-MS, LC-MS/MS and HPLC with multichannel UV detector. Synthetic hexaacetyl derivatives (8 and 9) were obtained by hydrogenation of 2 followed by acetylation with Ac_2O. The structure of 8 was confirmed by X-ray analysis. The acetylated extracts was indetified with authentic 8. Thus tetrahydro-D-monapterin(2) in T. Pyriformis were concluded to have (R)-configuration at the 6-position.
天然有機化合物討論会の論文
2000-10-01

72(P-61) 微生物中の微量テトラヒドロプテリンの絶対構造の決定(ポスター発表の部)

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