A SELECTIVE RECOGNITION MODE OF A NUCLEIC-ACID BASE BY AN AROMATIC AMINO-ACID - L-PHENYLALANINE-7-METHYLGUANOSINE 5'-MONOPHOSPHATE STACKING INTERACTION
A SELECTIVE RECOGNITION MODE OF A NUCLEIC-ACID BASE BY AN AROMATIC AMINO-ACID - L-PHENYLALANINE-7-METHYLGUANOSINE 5'-MONOPHOSPHATE STACKING INTERACTION
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DOI：
10.1093/nar/16.13.6175
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发表时间：
1988-07-11
影响因子：
14.9
通讯作者：
INOUE, M
中科院分区：
文献类型：
--
作者：
ISHIDA, T;DOI, M;INOUE, M
用X射线晶体学、核磁共振氢谱和能量计算方法研究了7-甲基鸟苷5“-单磷酸（m7 GMP）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）甲基化使m7 GMP分别朝向关于糖基和环外C（4“）·sbd.C（5”）键的反-gauche、gauche构象移动。在Phe的苯环和m7 GMP的鸟嘌呤碱基之间观察到的显著堆叠主要是由于鸟嘌呤碱基的N（7）季铵化。在阴离子羧基和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。目前的结果暗示了芳香族氨基酸作为选择性识别核酸碱基的标志的重要性。
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'').sbd.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) quarternization 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.