Stereochemistry of biopterin cofactor and facile methods for the determination of the stereochemistry of a biologically active 5,6,7,8-tetrahydropterin.
Stereochemistry of biopterin cofactor and facile methods for the determination of the stereochemistry of a biologically active 5,6,7,8-tetrahydropterin.
复制标题
生物蝶呤辅因子的立体化学和用于测定生物活性 5,6,7,8-四氢蝶呤立体化学的简便方法。
DOI：
10.1093/oxfordjournals.jbchem.a135401
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发表时间：
1985
影响因子：
2.7
通讯作者：
H. Iwasaki
中科院分区：
文献类型：
--
作者：
S. Matsuura;T. Sugimoto;S. Murata;Y. Sugawara;H. Iwasaki
（-）-四氢蝶呤是苯丙氨酸、酪氨酸和色氨酸羟化酶的辅助因子，通过x射线晶体分析确定其结构为(6R, 1' r,2')-6-（1',2'-二羟丙基）-5,6,7,8-四氢蝶呤。在pH为3.2的溶液中，(-)-四氢生物蝶呤的CD光谱在290 ~ 240 nm处呈现负棉花效应。以2-甲基四氢萘为模型化合物的CD分析支持了负棉花效应与6R构型的关系。利用CD光谱测定了各种具有生物活性的6-取代四氢蝶呤的C(6)位立体化学。在强阳离子交换柱上用高效液相色谱法测定了两个不对称中心C(6)和C（1’）的相对构型。
The structure of (-)-tetrahydrobiopterin, the cofactor for phenylalanine, tyrosine, and tryptophan hydroxylases, was determined as (6R, 1'R, 2'S)-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin by X-ray crystallographic analysis. The CD spectra of (-)-tetrahydrobiopterin exhibits a negative Cotton effect at 290-240 nm in pH 3.2 solution. The relationship of the negative Cotton effect and the 6R configuration was supported by the application of CD analysis with 2-methyltetrahydronaphthalene as a model compound. The stereochemistries at the C(6) position of various biologically active 6-substituted tetrahydropterins were determined from the CD spectra. The relative configuration of two asymmetric centers, C(6), and C(1'), was determined by HPLC analysis on a strong cation exchange column.