Lavergne Thomas, Janin Michaël, Dupouy Christelle, Vasseur Jean-Jacques, Debart Françoise
IBMM, University of Montpellier, France.
Curr Protoc Nucleic Acid Chem. 2010 Dec;Chapter 3:Unit3.19. doi: 10.1002/0471142700.nc0319s43.
The efficiency of chemical RNA synthesis has been radically improved by the use of pivaloyloxymethyl (PivOM) groups as 2'-protection, containing an acetal spacer that minimizes the steric effect of the ester group on the neighboring amidite during the coupling. However, the major benefit of the base-labile PivOM groups is their simple removal upon standard basic conditions applied to deprotect the RNA and release it from solid supports. Combined with standard acyl groups for nucleobases, cyanoethyl groups for phosphates, and base-cleavable linkers, PivOM groups make RNA deprotection as simple as DNA deprotection. Thus, no additional deprotection step with tedious desalting workup procedures is required, and RNA synthesis becomes as convenient and efficient as DNA synthesis.
通过使用新戊酰氧基甲基（PivOM）基团作为2'-保护基，化学RNA合成的效率得到了根本性的提高。该基团含有一个缩醛间隔基，可在偶联过程中将酯基对相邻亚磷酰胺的空间效应降至最低。然而，对碱不稳定的PivOM基团的主要优点是，在用于使RNA脱保护并将其从固相载体上释放的标准碱性条件下，它们可简单地被去除。与用于核苷碱基的标准酰基、用于磷酸酯的氰乙基以及可碱裂解的连接子相结合，PivOM基团使RNA脱保护与DNA脱保护一样简单。因此，无需额外的脱保护步骤以及繁琐的脱盐后处理程序，RNA合成变得与DNA合成一样方便和高效。
