Synthesis of a dodecaribonucleotide, GUAUCAAUAAUG, by use of "fully" protected ribonucleotide building blocks

• Published in: Journal of the American Chemical Society 1984-08, Vol.106 (16), p.4552-4557
• Main Authors: Kamimura, Takashi, Tsuchiya, Masahiko, Urakami, Kenichi, Koura, Koji, Sekine, Mitsuo, Shinozaki, Kazuko, Miura, Kinichiro, Hata, Tsujiaki
• Format: Article
• Language: English
• Subjects: Carbohydrates. Nucleosides and nucleotides; Chemistry; Exact sciences and technology; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Preparations and properties
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja00328a042

The fully protected ribonucleotide monomer units have been synthesized in excellent overall yields from unprotected riibonucleosides. Several carbamoyl groups were tested for protection of the guanosine base moiety. Finally, the diphenylcarbamoyl group was chosen and O super(6)-(diphenylcarbamoyl)-N super(2)-propionylguanosine was readily prepared in high yield and converted to the guanosine units. The uridine unit was prepared by the acylation of the previous unit with anisoyl chloride in the presence of i-Pr sub(2)EtN. In the case of the adenosine and cytidine units, the regioselective 2'-O-tetrahydropyranylation was involved in their syntheses. These "perfectly" protected monomer units have successfully been utilized in the synthesis of GUAUCAAUAAUG, a modified 5'-terminal structure, of brome mosaic virus (BMV) mRNA no. 4 filament. The dodecamer chain was elongated by fragment condensation from the 3'-5' direction.