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为什么核酸具有3',5'-磷酸二酯键？

Why do nucleic acids have 3'5' phosphodiester bonds?

作者信息

Dhingra M M, Sarma R H

出版信息

Nature. 1978 Apr 27;272(5656):798-801. doi: 10.1038/272798a0.

DOI:10.1038/272798a0
PMID:643069
Abstract

Details of the stereochemistry of the 2'5' and 3'5' dinucleoside monophosphates of polynucleotides have been delineated in aqueous solution using nuclear magnetic resonance spectroscopy. Incorporation of these experimentally determined geometries into the structure of polynucleotides reveals that the intrinsic spatial configurations of the 2'5' bonds cannot support helical structures whereas the geometries of 3'5' bonds allow the formation of helical configurations for RNA.

摘要

利用核磁共振光谱法已在水溶液中描绘出多核苷酸2'5'和3'5'二核苷单磷酸立体化学的细节。将这些通过实验确定的几何结构纳入多核苷酸结构中显示，2'5'键的固有空间构型无法支持螺旋结构，而3'5'键的几何结构则允许RNA形成螺旋构型。

相似文献

1
Why do nucleic acids have 3'5' phosphodiester bonds?为什么核酸具有3',5'-磷酸二酯键？
Nature. 1978 Apr 27;272(5656):798-801. doi: 10.1038/272798a0.
2
Stereochemistry of 2'-5' linked nucleic acids: crystal and molecular structure of ammonium adenylyl-2',5'-adenosine tetrahydrate: a core fragment of 2'-5' oligo A's produced by interferon induced adenylate synthetase.2'-5'连接核酸的立体化学：腺苷酰-2',5'-腺苷铵四水合物的晶体和分子结构：干扰素诱导的腺苷酸合成酶产生的2'-5'寡聚A的核心片段
J Biomol Struct Dyn. 1993 Feb;10(4):727-45. doi: 10.1080/07391102.1993.10508003.
3
Hydrogen-bonded complexes of the ribodinucleoside monophosphates in aqueous solution. Proton magnetic resonance studies.水溶液中核糖单磷酸核苷的氢键复合物。质子磁共振研究。
Biochemistry. 1976 Mar 23;15(6):1224-8. doi: 10.1021/bi00651a008.
4
Conformational studies of (2'-5') polynucleotides: theoretical computations of energy, base morphology, helical structure, and duplex formation.（2'-5'）多核苷酸的构象研究：能量、碱基形态、螺旋结构和双链形成的理论计算
Nucleic Acids Res. 1986 Jul 11;14(13):5461-79. doi: 10.1093/nar/14.13.5461.
5
The reactivity of phosphodiester bonds within linear single-stranded oligoribonucleotides is strongly dependent on the base sequence.线性单链寡核糖核苷酸内磷酸二酯键的反应活性强烈依赖于碱基序列。
Nucleic Acids Res. 2002 Jan 15;30(2):468-74. doi: 10.1093/nar/30.2.468.
6
Temperature dependence of the 31P chemical shifts of nucleic acids. A prode of phosphate ester torsional conformations.
Biochemistry. 1976 Aug 24;15(17):3796-803. doi: 10.1021/bi00662a023.
7
Helical structure of disodium 5'-guanosine monophosphate self-assembly in neutral solution.在中性溶液中，二钠 5'-鸟苷单磷酸自组装的螺旋结构。
J Am Chem Soc. 2009 Mar 11;131(9):3180-2. doi: 10.1021/ja809258y.
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Conformational properties of dinucleoside monophosphates in solution: dipurines and dipyrimidines.溶液中二磷酸核苷的构象性质：双嘌呤和双嘧啶。
Biochemistry. 1976 Aug 10;15(16):3627-39. doi: 10.1021/bi00661a034.
9
High-resolution nuclear magnetic resonance studies of double helical polynucleotides.双螺旋多核苷酸的高分辨率核磁共振研究。
Annu Rev Biophys Bioeng. 1977;6:477-523. doi: 10.1146/annurev.bb.06.060177.002401.
10
2'5'-linked polynucleotides do form a double-stranded helical structure: a result from the energy minimization study of A2'p5'A.2',5'-连接的多核苷酸确实形成双链螺旋结构：这是对A2'p5'A进行能量最小化研究的结果。
Biopolymers. 1986 Apr;25(4):729-52. doi: 10.1002/bip.360250414.

引用本文的文献

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Evaluating Geometric Definitions of Stacking for RNA Dinucleoside Monophosphates Using Molecular Mechanics Calculations.使用分子力学计算评估 RNA 二核苷酸单磷酸的堆积的几何定义。
J Chem Theory Comput. 2022 Jun 14;18(6):3637-3653. doi: 10.1021/acs.jctc.2c00178. Epub 2022 Jun 2.
2
2'/3' Regioselectivity of Enzyme-Free Copying of RNA Detected by NMR.NMR 检测到无酶 RNA 复制的 2'/3' 区域选择性。
Chembiochem. 2020 Jul 16;21(14):2013-2018. doi: 10.1002/cbic.202000014. Epub 2020 Mar 4.
3
Structural insights into RNA duplexes with multiple 2΄-5΄-linkages.
对具有多个2΄-5΄连接的RNA双链体的结构见解。
Nucleic Acids Res. 2017 Apr 7;45(6):3537-3546. doi: 10.1093/nar/gkw1307.
4
Structural insights into the effects of 2'-5' linkages on the RNA duplex.对 2'-5' 键连接对 RNA 双链体影响的结构见解。
Proc Natl Acad Sci U S A. 2014 Feb 25;111(8):3050-5. doi: 10.1073/pnas.1317799111. Epub 2014 Feb 10.
5
The 2-5A system: modulation of viral and cellular processes through acceleration of RNA degradation.2-5A系统：通过加速RNA降解来调节病毒和细胞过程。
Pharmacol Ther. 1998 May;78(2):55-113. doi: 10.1016/s0163-7258(97)00167-8.
6
Comparative spectroscopic, calorimetric, and computational studies of nucleic acid complexes with 2',5"-versus 3',5"-phosphodiester linkages.具有2',5"-与3',5"-磷酸二酯键的核酸复合物的比较光谱、量热和计算研究。
Proc Natl Acad Sci U S A. 1993 Nov 15;90(22):10568-72. doi: 10.1073/pnas.90.22.10568.
7
Recognition and catalysis in nucleic acid chemistry.核酸化学中的识别与催化
Proc Natl Acad Sci U S A. 1993 Feb 15;90(4):1201-7. doi: 10.1073/pnas.90.4.1201.
8
X-ray structure of a dinucleoside monophosphate A2'p5'C that contains a 2'-5' link found in (2'-5')oligo(A)s induced by interferons: single-stranded helical conformation of 2'-5'-linked oligonucleotides.一种含有2'-5'连接的二核苷酸单磷酸A2'p5'C的X射线结构，该连接存在于由干扰素诱导产生的(2'-5')寡聚腺苷酸中：2'-5'连接的寡核苷酸的单链螺旋构象。
Proc Natl Acad Sci U S A. 1982 Dec;79(23):7292-6. doi: 10.1073/pnas.79.23.7292.
9
Conformational studies of (2'-5') polynucleotides: theoretical computations of energy, base morphology, helical structure, and duplex formation.（2'-5'）多核苷酸的构象研究：能量、碱基形态、螺旋结构和双链形成的理论计算
Nucleic Acids Res. 1986 Jul 11;14(13):5461-79. doi: 10.1093/nar/14.13.5461.
10
Visualisation of a 2'-5' parallel stranded double helix at atomic resolution: crystal structure of cytidylyl-2',5'-adenosine.2'-5'平行链双螺旋的原子分辨率可视化：胞苷-2',5'-腺苷的晶体结构
Nucleic Acids Res. 1991 Jan 25;19(2):379-84. doi: 10.1093/nar/19.2.379.