In order to investigate the mode of interaction between the N-quarternized cytosine base and the aromatic amino acid, the crystal structure of the 3-methyl-cytidine-5'-monophosphate:tryptamine complex was analyzed by X-ray diffraction. The complex crystals were stabilized by extensive hydrogen bond formations in which eight independent water molecules per complex pair participated. A prominent stacking interaction, characterized by a parallel alignment of both rings with a separation distance of ca. 3.4 A, was observed between the cytosine base and the indole ring. Combining the present results with X-ray crystallographic data on the adenine--and guanine--aromatic amino acid interactions, we summarize the structural characteristics observed in the stacking interaction of the N-quarternized nucleic acid base with the aromatic amino acid and discuss their biological implications, especially in connection with the significance of N-protonation of nucleic acid base for selective recognition by protein.

译文

:为了研究N-季铵化的胞嘧啶碱基与芳族氨基酸之间的相互作用方式,通过X射线衍射分析了3-甲基胞苷-5'-单磷酸酯:色胺的配合物的晶体结构。复杂的晶体通过广泛的氢键形成而稳定,其中每个复杂对有八个独立的水分子参与。突出的堆叠相互作用,其特征在于两个环的平行排列的间隔距离为ca。在胞嘧啶碱基和吲哚环之间观察到3.4A。将当前结果与腺嘌呤-鸟嘌呤-芳族氨基酸相互作用的X射线晶体学数据相结合,我们总结了在N-季铵化核酸碱基与芳族氨基酸的堆叠相互作用中观察到的结构特征,并讨论了它们的结构特征。生物学意义,特别是与核酸碱基的N质子化对于蛋白质选择性识别的意义有关。

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