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Problems of the Synthesis of Oligonucleotide Derivatives in the Realization of the Anchimeric Effect
Russian Journal of Bioorganic Chemistry ( IF 1 ) Pub Date : 2021-04-26 , DOI: 10.1134/s1068162021020096
E. S. Dyudeeva , A. S. Pavlova , M. S. Kupryushkin , D. V. Pyshnyi , I. A. Pyshnaya

Abstract

It has been found that the presence of a free OH group at the 3'-terminal residue of the substituted ethylene glycol fragment in a phosphoryl guanidine oligodeoxyribonucleotide derivative is a factor that determines the instability of the structure of the target oligonucleotide product under the conditions of a standard deblocking protocol. It has been shown that the main by-products of the realization of the anchimeric effect of the OH group are the products of the transesterification of the phosphoryl guanidine (PG) unit carrying the O-substituted ethylene glycol residue. The data of the mass spectrometry analysis indicate that, under alkaline conditions, the accumulation of derivatives devoid of the N,N,N',N'-substituted guanidine residue (1,3-dimethylimidazolidin-2-imine, DMI) or the entire 3'-terminal PG-containing nonnucleotide unit occurs.



中文翻译:

实现嵌合效应的寡核苷酸衍生物的合成问题

摘要

已经发现在磷酸胍胍寡脱氧核糖核苷酸衍生物中的取代的乙二醇片段的3'-末端残基上存在游离的OH基团是决定目标寡核苷酸产物在以下条件下结构不稳定的因素。标准解块协议。已经表明,实现OH基团的嵌合作用的主要副产物是带有O-取代的乙二醇残基的磷酰胍(PG)单元的酯交换反应的产物。质谱分析的数据表明,在碱性条件下,缺乏NNN ',N的衍生物的积累发生′-取代的胍残基(1,3-二甲基咪唑啉丁-2-亚胺,DMI)或整个含3′-末端PG的非核苷酸单元。

更新日期:2021-04-27
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