3-methylinosine: Synthesis, acid-catalyzed cleavage of the glycosyl bond, base-catalyzed ring-opening, and hydrogenation of the pyrimidine ring

✍ Scribed by Taisuke Itaya; Hiroo Matsumoto

• Book ID: 104246160
• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 326 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95136-6

✦ Synopsis

The natural occurrence of 3-alkylpurine ribosides has not been reported, although many modified nucleosides are known to occur in RNA: However, the proposed structures' for the fluorescent Y nucleosides [wyosine (Ia); wybutosine (Ib); wybutoxosine (Ic)] ,2b which were found in tRNAPhes,3 show that they are the derivatives of 3-methylguanosine (II). Nakatsuka and Goto recently mentioned the synthesis of Ia and II .4 We also reported a simpler synthesis of II? The prominent feature common between I and II is unusual lability of the nucleosidic linkage under acidic conditions.2'3b14'5 For elucidation of questions of such easy acidic hydrolysis, there is a need for some other 3-methylpurine ribosides. In this communication, we wish to report the synthesis and chemical properties of hitherto unknown 3-methylinosine (Via) .