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Nucleic Acids Research, 1984, Vol. 12, No. 6 2939-2954
© 1984

CHEMISTRY

Chemical synthesis of the 5'-terminal part bearing cap structure of messenger RNA of cytoplasmic polyhedrosis virus (CPV): m7G5' pppAmpG and m7G5pppAmpGpU

Kazuo Yamaguchi, Iwao Nakagawa, Mitsuo Sekine, Tsujiaki Hata*, Kunitada Shimotohno+, Michiyo Hiruta+ and Kin-ichiro Miura+

Department of Life Chemistry, Tokyo Institute of Technology Nagatsuta, Midoriku, Yokohama 227 +National Institute of Genetics Mishima 411, Japan

*To whom correspondence should be addressed

Received December 23, 1983. Revised February 24, 1984. Accepted February 24, 1984.

The 5'-terminal structures of mRNA bearing the so-called ‘cap,’ from cytoplasmic polyhedrosis virus (CPV), m7 G5 pppAmpG and m7 G5 pppAmpGpU, were first chemically synthesized. S,S-Di(4-methoxyphenyl) N 6-benzoyl-2'-O-methyladenosine 5'-phosphorodithioate ((ArS)2pAmbz) was prepared by phosphorylation of the 5'-hydroxyl group of N6 -benzoyl-2'-O-methyladenosine with S,S-di(4-methoxyphenyl) phosphorpdithioate by TPS. By the triester approach using (ArS)-2pAmbz 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)ppm 7G) 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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