Efimov V A, Kalinkina A L, Chakhmakhcheva O G
Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow.
Nucleic Acids Res. 1993 Nov 25;21(23):5337-44. doi: 10.1093/nar/21.23.5337.
Dipentafluorophenyl carbonate has been successfully used as condensing agent for the internucleotide bond formation in the synthesis of oligonucleotides via H-phosphonate approach. The mechanism of a nucleotide component activation with this reagent has been investigated with the help of 31P NMR spectroscopy. It was shown that preactivation of deoxynucleoside H-phosphonate with dipentafluorophenyl carbonate has no influence on the efficiency of the synthesis. This reagent is highly reactive, nonhygroscopic and stable on storage at room temperature. The effectiveness of dipentafluorophenyl carbonate in the oligonucleotide chemistry has been demonstrated in the solid-phase synthesis of 10-50-mers on 0.2, 1 and 10 mumol scales. The use of this reagent for the derivatisation of polymer supports as well as for the synthesis of oligonucleotide conjugates with polyethylene glycol and a lipid is described.
五氟苯基碳酸酯已成功用作通过H-膦酸酯法合成寡核苷酸时形成核苷酸间键的缩合剂。借助31P NMR光谱研究了该试剂激活核苷酸组分的机制。结果表明,用五氟苯基碳酸酯对脱氧核苷H-膦酸酯进行预活化对合成效率没有影响。该试剂具有高反应活性、不吸湿且在室温下储存稳定。在0.2、1和10微摩尔规模的10 - 50聚体的固相合成中证明了五氟苯基碳酸酯在寡核苷酸化学中的有效性。描述了该试剂用于聚合物载体的衍生化以及用于合成与聚乙二醇和脂质的寡核苷酸缀合物。