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Synthesis and Structural Analysis of N3-Methyluridine and 2’-Alkoxy/Fluoro-N3-Methyluridine Nucleosides by Using NMR Spectroscopy, X-Ray Crystallography, and Computational Methods
ChemistrySelect ( IF 1.9 ) Pub Date : 2023-06-22 , DOI: 10.1002/slct.202301858
Avijit Sahoo 1 , Gourav Das 1 , Nishant Kumar Choudhary 1 , S. Harikrishna 2 , Kiran R. Gore 1
Affiliation  

The X-ray data confirms the C2’-endo conformation for N3-Methyluridine, whereas all the 2’-substituted N3-methyluridine analogs tunes sugar conformation to C3’-endo predominantly. The stereoelectronic effects like anomeric and hyperconjugation effects influence the sugar puckering towards the North conformation due to the presence of electron-withdrawing 2’-alkoxy and fluoro substituents.

中文翻译:

利用核磁共振波谱、X 射线晶体学和计算方法合成 N3-甲基尿苷和 2'-烷氧基/氟-N3-甲基尿苷核苷并进行结构分析

X射线数据证实了N 3 -甲基尿苷的C2'-构象,而所有2'-取代的N 3 -甲基尿苷类似物主要将糖构象调整为C3'-内构象。由于吸电子 2'-烷氧基和氟取代基的存在,异头效应和超共轭效应等立体电子效应影响糖向North构象折叠。
更新日期:2023-06-22
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