Pitsch Stefan, Weiss Patrick A
Institut de Chimie Organique, EPFL, Lausanne, Switzerland.
Curr Protoc Nucleic Acid Chem. 2002 Feb;Chapter 3:Unit 3.8. doi: 10.1002/0471142700.nc0308s07.
The [(triisopropylsilyl)oxy]methyl (TOM) group is a useful protecting group for the 2'-OH of ribonucleosides to be used for oligoribonucleotide synthesis by the phosphoramidite method. It is completely stable to all reaction conditions applied during assembly and the first deprotection step. It does not interfere with the coupling reaction and leads to very good coupling yields under DNA-coupling conditions. The final cleavage occurs quantitatively without concomitant destruction of the RNA product. This unit describes the synthesis of TOM-phosphoramidites from 2'-O-TOM-5'-O-dimethoxytrityl-N-acetyl ribonucleosides, oligoribonucleotide assembly on an automated DNA synthesizer, and subsequent deprotection. Preparation of the TOM-protected ribonucleosides is presented elsewhere in the series.
[(三异丙基甲硅烷基)氧基]甲基（TOM）基团是用于通过亚磷酰胺法合成寡核糖核苷酸的核糖核苷2'-OH的有用保护基团。它在组装和第一步脱保护步骤中应用的所有反应条件下都完全稳定。它不干扰偶联反应，并在DNA偶联条件下产生非常好的偶联产率。最终裂解定量发生，且不会伴随RNA产物的破坏。本单元描述了由2'-O-TOM-5'-O-二甲氧基三苯甲基-N-乙酰基核糖核苷合成TOM-亚磷酰胺、在自动DNA合成仪上进行寡核糖核苷酸组装以及随后的脱保护。TOM保护的核糖核苷的制备在本系列的其他地方介绍。
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