一种通用且高效的合成 5'-标记嘌呤核苷的膦酰胺的方法。
A general and efficient approach to synthesize the phosphoramidites of 5'- labeled purine nucleosides.
机构信息
Department of Biochemistry & Molecular Biology, University of Chicago, Chicago, Illinois, USA.
Department of Chemistry, University of Chicago, Chicago, Illinois, USA.
出版信息
Nucleosides Nucleotides Nucleic Acids. 2023;42(11):930-943. doi: 10.1080/15257770.2023.2218421. Epub 2023 May 26.
5'- labeled RNA oligos are important probes to investigate the mechanism of 2'--transphosphorylation reactions. Here we describe a general and efficient synthetic approach to the phosphoramidite derivatives of 5'- labeled nucleosides starting from the corresponding commercially available 5'--DMT protected nucleosides. Using this method, we prepared 5'--guanosine phosphoramidite in 8 steps (13.2% overall yield), 5'-adenosine phosphoramidite in 9 steps (10.1% overall yield) and 5'--2'-deoxyguanosine phosphoramidite in 6 steps (12.8% overall yield). These 5'- labeled phosphoramidites can be incorporated into RNA oligos by solid phase synthesis for determination of heavy atom isotope effects in RNA 2'--transphosphorylation reactions.
5′-标记 RNA 寡核苷酸是研究 2′-转磷酸反应机制的重要探针。在这里，我们描述了一种从相应的商业上可获得的 5′-DMT 保护核苷起始的 5′-标记核苷的磷酰胺衍生物的通用且有效的合成方法。使用该方法，我们以 8 步（总收率为 13.2%）制备了 5′-鸟苷磷酰胺，以 9 步（总收率为 10.1%）制备了 5′-腺苷磷酰胺，并以 6 步（总收率为 12.8%）制备了 5′-2′-脱氧鸟苷磷酰胺。这些 5′-标记的磷酰胺可以通过固相合成掺入 RNA 寡核苷酸中，以确定 RNA 2′-转磷酸反应中的重原子同位素效应。
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