芳香族氨基酸对核酸碱基的选择性识别模式：L-苯丙氨酸与7-甲基鸟苷5'-单磷酸的堆积相互作用。
A selective recognition mode of a nucleic acid base by an aromatic amino acid: L-phenylalanine-7-methylguanosine 5'-monophosphate stacking interaction.
作者信息
Ishida T, Doi M, Inoue M
机构信息
Laboratory of Physical Chemistry, Osaka University of Pharmaceutical Sciences, Japan.
出版信息
Nucleic Acids Res. 1988 Jul 11;16(13):6175-90. doi: 10.1093/nar/16.13.6175.
Abstract
The conformation of 7-methylguanosine 5'-monophosphate (m7GMP) and its interaction with L-phenylalanine (Phe) have been investigated by X-ray crystallographic, 1H-nuclear magnetic resonance, and energy calculation methods. The N(7) methylation of the guanine base shifts m7GMP toward an anti--gauche, gauche conformation about the glycosyl and exocyclic C(4')-C(5') bonds, respectively. The prominent stacking observed between the benzene ring of Phe and guanine base of m7GMP is primarily due to the N(7) guarternization of the guanine base. The formation of a hydrogen bonding pair between the anionic carboxyl group and the guanine base further stabilizes this stacking interaction. The present results imply the importance of aromatic amino acids as a hallmark for the selective recognition of a nucleic acid base.
摘要
通过X射线晶体学、1H核磁共振和能量计算方法，研究了7-甲基鸟苷5'-单磷酸（m7GMP）的构象及其与L-苯丙氨酸（Phe）的相互作用。鸟嘌呤碱基的N(7)甲基化分别使m7GMP围绕糖苷键和环外C(4')-C(5')键向反式- gauche、gauche构象转变。在Phe的苯环与m7GMP的鸟嘌呤碱基之间观察到的显著堆积主要是由于鸟嘌呤碱基的N(7)季铵化。阴离子羧基与鸟嘌呤碱基之间形成氢键对进一步稳定了这种堆积相互作用。目前的结果表明芳香族氨基酸作为核酸碱基选择性识别标志的重要性。
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