细胞质多角体病毒（CPV）信使核糖核酸（mRNA）5′末端带有帽结构部分的化学合成：m7G5′pppAmpG和m7G5′pppAmpGpU
Chemical synthesis of the 5'-terminal part bearing cap structure of messenger RNA of cytoplasmic polyhedrosis virus (CPV): m7G5'pppAmpG and m7G5'pppAmpGpU.
作者信息
Yamaguchi K, Nakagawa I, Sekine M, Hata T, Shimotohno K, Hiruta M, Miura K
出版信息
Nucleic Acids Res. 1984 Mar 26;12(6):2939-54. doi: 10.1093/nar/12.6.2939.
The 5'-terminal structures of mRNA bearing the so-called 'cap' from cytoplasmic polyhedrosis virus (CPV), m7G5' pppAmpG and m7G5' pppAmpGpU, were first chemically synthesized. S,S-Di(4-methoxyphenyl) N6-benzoyl-2'-O-methyladenosine 5'-phosphorodithioate ((ArS) 2pAbmz) was prepared by phosphorylation of the 5'-hydroxyl group of N6-benzoyl-2'-O-methyladenosine with S,S-di(4-methoxyphenyl) phosphorodithioate by TPS. By the triester approach using (ArS) 2pAbmz as starting material, the protected dinucleotide and trinucleotide bearing 5'-phosphate group were synthesized. The protective groups of the dinucleotide and trinucleotide were removed to obtain pAmpG and pAmpGpU, respectively. By the reaction of a capping agent ((PhS) ppm7G) with pAmpG and pAmpGpU in the presence of silver nitrate or iodine. The 5'-terminal structure of the messenger RNA strand of CPV which was labelled isotopically, was confirmed completely as m7G5' pppAmGpU by cochromatography with the materials chemically synthesized here.
首次化学合成了来自细胞质多角体病毒（CPV）的带有所谓“帽”结构的mRNA的5'-末端结构，即m7G5' pppAmpG和m7G5' pppAmpGpU。通过硫代磷酸三苯酯（TPS）用S，S-二（4-甲氧基苯基）硫代磷酸酯对N6-苯甲酰基-2'-O-甲基腺苷的5'-羟基进行磷酸化反应，制备了S，S-二（4-甲氧基苯基）N6-苯甲酰基-2'-O-甲基腺苷5'-硫代磷酸酯（（ArS）2pAbmz）。以（ArS）2pAbmz为起始原料，采用三酯法合成了带有5'-磷酸基团的保护型二核苷酸和三核苷酸。分别除去二核苷酸和三核苷酸的保护基团，得到pAmpG和pAmpGpU。通过封端剂（（PhS）ppm7G）与pAmpG和pAmpGpU在硝酸银或碘存在下反应。通过与这里化学合成的物质进行共色谱分析，完全证实了经同位素标记的CPV信使RNA链的5'-末端结构为m7G5' pppAmGpU。
Zotero 插件