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-四分之一化胞嘧啶碱与芳香族氨基酸之间的相互作用模式,通过x射线衍射分析了3-甲基胞苷-5 '-单磷酸: 色胺复合物的晶体结构。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其中。在胞嘧啶碱和吲哚环之间观察到显著的堆叠相互作用,其特征是两个环平行排列,分离距离约3.4 A。结合目前的结果与腺嘌呤-和鸟嘌呤-芳香族氨基酸相互作用的x射线晶体学数据,我们总结了在N-四分之一化核酸碱基与芳香族氨基酸的堆叠相互作用中观察到的结构特征,并讨论了它们的生物学意义,特别是与核酸碱基的N-质子化对蛋白质选择性识别的意义有关。

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