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首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Influence of fluorine substitution on the molecular conformation of 3′‐deoxy‐3′‐fluoro‐5‐methyluridine
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Influence of fluorine substitution on the molecular conformation of 3′‐deoxy‐3′‐fluoro‐5‐methyluridine

机译：氟取代对3'-脱氧-3'-氟-5-甲基嘌呤的分子构象的影响

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Fluorine substitutions on the furanose ring of nucleosides are known to strongly influence the conformational properties of oligonucleotides. In order to assess the effect of fluorine on the conformation of 3′‐deoxy‐3′‐fluoro‐5‐methyluridine ( R T F ), C 10 H 13 FN 2 O 5 , we studied its stereochemistry in the crystalline state using X‐ray crystallography. The compound crystallizes in the chiral orthorhombic space group P 2 1 2 1 2 1 and contains two symmetry‐independent molecules ( A and B ) in the asymmetric unit. The furanose ring in molecules A and B adopts conformations between envelope ( 2 E, 2′‐ endo , P ?= 162°) and twisted ( 2 T 3 , 2′‐ endo and 3′ exo , P ?= 180°), with pseudorotation phase angles ( P ) of 164.3 and 170.2°, respectively. The maximum puckering amplitudes, ν max , for molecules A and B are 38.8 and 36.1°, respectively. In contrast, for 5‐methyluridine ( R T OH ), the value of P is 21.2°, which is between the 3 E (3′‐ endo , P ?= 18.0°) and 3 T 4 (3′‐ endo and 4′‐ exo , P ?= 36°) conformations. The value of ν max for R T OH is 41.29°. Molecules A and B of R T F generate respective helical assemblies across the crystallographic 2 1 ‐screw axis through classical N—H…O aand O—H…O hydrogen bonds supplemented by C—H…O contacts. Adjacent parallel helices of both molecules are linked to each other via O—H…O and O…π interactions.
机译：已知核苷酸呋喃环呋喃环氟取代强烈影响寡核苷酸的构象性质。为了评估氟对3'-脱氧-3'-氟-5-甲基嘌呤（RTF）的构象的影响，C 10 H 13 Fn 2 O 5，我们使用X射线研究了结晶状态的立体化学晶体学。该化合物在手性正交间空间组P 2 11 2 11中结晶，并在不对称单元中含有两个对称依赖性分子（A和B）。分子A和B中的呋喃糖环采用包膜（2 e，2'- endo，p≤162°）之间的构象，并扭曲（2 t 3,2'- endo和3'exo，p？= 180°），分别为164.3和170.2°的伪体相角（p）。分子A和B的最大点褶皱幅度，νmax为38.8和36.1°。相反，对于5-甲基嘌呤（RT OH），P的值是21.2°，其在3e（3'- endo，p≤18.0°）和3 t 4（3'- endo和4'之间 - exo，p？= 36°）构象。 R T OH的νmax值为41.29°。 R T F的分子A和B通过透视N-H ... O AAND O-H ... O AAND O-H ... O AAND O-H ... O氢键来产生各自的螺旋组件。通过C-H ... O触点。两种分子的相邻平行螺旋通过O-H ... O和O ...π相互作用彼此连接。

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