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1
A selective recognition mode of a nucleic acid base by an aromatic amino acid: L-phenylalanine-7-methylguanosine 5'-monophosphate stacking interaction.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。
Nucleic Acids Res. 1988 Jul 11;16(13):6175-90. doi: 10.1093/nar/16.13.6175.
2
Stacking and hydrogen bonding interactions between phenylalanine and guanine nucleotide: crystal structure of L-phenylalanine-7-methylguanosine-5'-monophosphate complex.
Biochem Biophys Res Commun. 1986 Apr 14;136(1):294-9. doi: 10.1016/0006-291x(86)90908-3.
3
The specific guanine binding site of the ribonuclease T1 family enzymes and of G-proteins is modeled in the cocrystal formed by 7-methylguanosine-5'-phosphate and phenylalanine.核糖核酸酶T1家族酶和G蛋白的特定鸟嘌呤结合位点，在由7-甲基鸟苷-5'-磷酸和苯丙氨酸形成的共晶体中得到了模拟。
J Biochem. 1989 Aug;106(2):189-91. doi: 10.1093/oxfordjournals.jbchem.a122829.
4
Proton nuclear magnetic resonance study on the aromatic amino acid-guanine nucleotide system: effect of base methylation on the stacking interaction with tyrosine and phenylalanine.芳香族氨基酸 - 鸟嘌呤核苷酸系统的质子核磁共振研究：碱基甲基化对与酪氨酸和苯丙氨酸堆积相互作用的影响。
Chem Pharm Bull (Tokyo). 1989 Jan;37(1):1-4. doi: 10.1248/cpb.37.1.
5
Prominent stacking interaction with aromatic amino acid by N-quarternization of nucleic acid base: X-ray crystallographic characteristics and biological implications.通过核酸碱基的N-季铵化与芳香族氨基酸形成显著的堆积相互作用：X射线晶体学特征及生物学意义。
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6
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Biochemistry. 1987 Jul 14;26(14):4372-80. doi: 10.1021/bi00388a028.
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Base stacking of simple mRNA cap analogues. Association of 7,9-dimethylguanine, 7-methylguanosine and 7-methylguanosine 5'-monophosphate with indole and purine derivatives in aqueous solution.
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Indole ring binds to 7-methylguanine base by pi-pi stacking interaction. Crystal structure of 7-methylguanosine 5'-monophosphate-tryptamine complex.吲哚环通过π-π堆积相互作用与7-甲基鸟嘌呤碱基结合。7-甲基鸟苷5'-单磷酸-色胺复合物的晶体结构。
FEBS Lett. 1986 Jan 20;195(1-2):57-60. doi: 10.1016/0014-5793(86)80129-6.
10
Peptide hairpins with strand segments containing alpha- and beta-amino acid residues: cross-strand aromatic interactions of facing Phe residues.具有包含α-和β-氨基酸残基的链段的肽发夹：相对苯丙氨酸残基的跨链芳香族相互作用。
Biopolymers. 2005;80(6):787-99. doi: 10.1002/bip.20294.

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Structural basis for substrate discrimination by repair enzyme, AlkB.修复酶AlkB对底物进行识别的结构基础。
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Large-scale induced fit recognition of an m(7)GpppG cap analogue by the human nuclear cap-binding complex.人源细胞核帽结合复合物对m(7)GpppG帽类似物的大规模诱导契合识别
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ELECTRON-DONOR AND -ACCEPTOR PROPERTIES OF BIOLOGICALLY IMPORTANT PURINES, PYRIMIDINES, PTERIDINES, FLAVINS, AND AROMATIC AMINO ACIDS.生物重要嘌呤、嘧啶、蝶啶、黄素及芳香族氨基酸的电子供体和受体性质
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Inter- and intramolecular stacking interaction between indole and adeninium rings.
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The stacking interactions in 7-methylguanine-tryptophan systems, a model study for the interaction between the 'cap' structure of mRNA and its binding protein.7-甲基鸟嘌呤-色氨酸体系中的堆积相互作用，一项关于mRNA“帽”结构与其结合蛋白之间相互作用的模型研究。
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Interactions between functional groups in protein-nucleic acid associations.蛋白质-核酸结合中官能团之间的相互作用。
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Conformational analysis of the sugar ring in nucleosides and nucleotides. A new description using the concept of pseudorotation.核苷和核苷酸中糖环的构象分析。一种使用假旋转概念的新描述。
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Molecular orbital calculations on the conformation of nucleic acids and their constituents. VI. Conformation about the exocyclic C(4')-C(5') bond in alpha-nucleosides.核酸及其成分构象的分子轨道计算。VI. α-核苷中外环C(4')-C(5')键的构象
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Nuclear magnetic resonance studies of 5'-ribo- and deoxyribonucleotide structures in solution.溶液中5'-核糖核苷酸和脱氧核糖核苷酸结构的核磁共振研究。
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Structural analysis of the messenger RNA cap-binding protein. Presence of phosphate, sulfhydryl, and disulfide groups.信使核糖核酸帽结合蛋白的结构分析。磷酸基团、巯基和二硫键的存在。
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Stacking and hydrogen bonding interactions between phenylalanine and guanine nucleotide: crystal structure of L-phenylalanine-7-methylguanosine-5'-monophosphate complex.
Biochem Biophys Res Commun. 1986 Apr 14;136(1):294-9. doi: 10.1016/0006-291x(86)90908-3.

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.

DOI:10.1093/nar/16.13.6175
PMID:3399389
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC336855/
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。