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肟键形成作为制备3',5'-双功能化寡脱氧核糖核苷酸的有效化学工具。

The oxime bond formation as an efficient chemical tool for the preparation of 3',5'-bifunctionalised oligodeoxyribonucleotides.

作者信息

Edupuganti Om Prakash, Renaudet Olivier, Defrancq Eric, Dumy Pascal

机构信息

LEDSS, UMR CNRS 5616, ICMG FR2607, Université Joseph Fourier, BP 53, 38041 Grenoble 9, France.

出版信息

Bioorg Med Chem Lett. 2004 Jun 7;14(11):2839-42. doi: 10.1016/j.bmcl.2004.03.053.

Abstract

The simultaneous conjugation of peptides or carbohydrates at the 3'- and 5'-end of oligodeoxyribonucleotides was achieved very efficiently through chemoselective oxime bond formation. The method employs bifunctionalised oligonucleotides in single step without the need of protection strategy, under mild acidic conditions. The conjugates were obtained in high yields by reacting an oxyamine containing reporter groups (peptide, mono- and disaccharide) with an oligonucleotide carrying an aldehyde at each extremity.

摘要

通过化学选择性肟键的形成,可非常高效地实现寡脱氧核糖核苷酸3'-和5'-末端肽或碳水化合物的同时共轭。该方法在温和酸性条件下,采用双功能化寡核苷酸一步完成,无需保护策略。通过使含有报告基团(肽、单糖和二糖)的氧胺与在每个末端带有醛基的寡核苷酸反应,可高产率获得共轭物。

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