Abstract
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.
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- Adamiak R. W., Biala E., Grześkowiak, Kierzek R., Kraszewski A., Markiewicz W. T., Stawiński J., Wiewiórowski Nucleoside 3'-phosphotriesters as key intermediates for the oligoribonucleotide synthesis. IV. New method for removal of 2,2,2-trichloroethyl group and 31P NMR as a new tool for analysis of deblocking of internucleotide phosphate protecting groups. Nucleic Acids Res. 1977 Jul;4(7):2321–2329. doi: 10.1093/nar/4.7.2321. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Furuichi Y., LaFiandra A., Shatkin A. J. 5'-Terminal structure and mRNA stability. Nature. 1977 Mar 17;266(5599):235–239. doi: 10.1038/266235a0. [DOI] [PubMed] [Google Scholar]
- Furuichi Y., Miura K. A blocked structure at the 5' terminus of mRNA from cytoplasmic polyhedrosis virus. Nature. 1975 Jan 31;253(5490):374–375. doi: 10.1038/253374a0. [DOI] [PubMed] [Google Scholar]
- Katagiri N., Itakura K., Narang S. A. The use of arylsulfonyltriazoles for the synthesis of oligonucleotides by the triester approach. J Am Chem Soc. 1975 Dec 10;97(25):7332–7337. doi: 10.1021/ja00858a021. [DOI] [PubMed] [Google Scholar]
- Miura K. The cap structure in eukaryotic messenger RNA as a mark of a strand carrying protein information. Adv Biophys. 1981;14:205–238. [PubMed] [Google Scholar]
- Robins M. J., Naik S. R., Lee A. S. Nucleic acid related compounds. 12. The facile and high-yield stannous chloride catalyzed monomethylation of the cis-glycol system of nucleosides by diazomethane. J Org Chem. 1974 Jun 28;39(13):1891–1899. doi: 10.1021/jo00927a022. [DOI] [PubMed] [Google Scholar]
- Shatkin A. J. Capping of eucaryotic mRNAs. Cell. 1976 Dec;9(4 Pt 2):645–653. doi: 10.1016/0092-8674(76)90128-8. [DOI] [PubMed] [Google Scholar]
- Shimotohno K., Kodama Y., Hashimoto J., Miura K. I. Importance of 5'-terminal blocking structure to stabilize mRNA in eukaryotic protein synthesis. Proc Natl Acad Sci U S A. 1977 Jul;74(7):2734–2738. doi: 10.1073/pnas.74.7.2734. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Shimotohno K., Miura K. i. The process of formation of the 5' -terminal modified structure in messenger RNA of cytoplasmic polyhedrosis virus. FEBS Lett. 1976 Apr 15;64(1):204–208. doi: 10.1016/0014-5793(76)80284-0. [DOI] [PubMed] [Google Scholar]
- Weber H., Khorana H. G. CIV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxynucleotide corresponding to the nucleotide sequence 21 to 40. J Mol Biol. 1972 Dec 28;72(2):219–249. doi: 10.1016/0022-2836(72)90147-7. [DOI] [PubMed] [Google Scholar]
- Zan-Kowalczewska M., Bretner M., Sierakowska H., Szczesna E., Filipowicz W., Shatkin A. J. Removal of 5'-terminal m7G from eukaryotic mRNAs by potato nucleotide pyrophosphatase and its effect on translation. Nucleic Acids Res. 1977 Sep;4(9):3065–3081. doi: 10.1093/nar/4.9.3065. [DOI] [PMC free article] [PubMed] [Google Scholar]