Oligonucleotide conjugates are widely used as therapeutic drugs, gene analysis, and diagnostic tools. A critical step in the biologically relevant oligonucleotide conjugates is the design and synthesis of functional molecules that connect oligonucleotide with ligands. Here, we report the synthesis and application for oligonucleotide functionalization of novel tethers based on aminomethyl and mercaptomethyl sugar derivatives. Starting from a common cyano sugar precursor, three novel phosphoramidites have been prepared in the two α- and β-anomeric forms. The mercaptomethyl sugar was protected with the S-acetyl group, while two different protecting groups have been developed for the aminomethyl sugar. These two protecting groups are orthogonal, as they can be removed independently using photolysis or ammonolysis. This combination allowed the introduction of two different ligands in a single oligonucleotide.

中文翻译：

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含有 1-氨基甲基或 1-巯基甲基-2-脱氧-d-呋喃核糖的寡核苷酸：合成、纯化、表征和与荧光团和脂质的结合

寡核苷酸偶联物广泛用作治疗药物、基因分析和诊断工具。生物学相关寡核苷酸偶联物的一个关键步骤是设计和合成将寡核苷酸与配体连接的功能分子。在这里，我们报告了基于氨基甲基和巯基甲基糖衍生物的新型系链的寡核苷酸功能化的合成和应用。从常见的氰基糖前体开始，三种新型亚磷酰胺已制备成两种 α-和 β-异头异构体形式。巯甲基糖被S保护-乙酰基，而已经为氨基甲基糖开发了两种不同的保护基团。这两个保护基团是正交的，因为它们可以使用光解或氨解独立去除。这种组合允许在单个寡核苷酸中引入两种不同的配体。