Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid

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概要

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• Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (5a) with CNBr in acetate buffer gave the 5-cyanomethylamino derivative 6a, which was cyclized to 3-methyl-guanosine (7) in the presence of NaOEt. Cyclocondensation of 7 with bromoacetone in the presence of K_2CO_3 provided 3-β-D-ribofuranosylwye (2), the most probable structure for the fluorescent nucleoside from Torulopsis utilis phenylalanine transfer ribonucleic acid (tRNA^<Phe>). The glycosidic bonds of 2 and 7 have been shown to be unusually subject to cleavage under either acidic or basic conditions, but proved to be less labile under neutral conditions, as had been reported. The base moiety of 2 is also cleaved under basic conditions.

• 公益社団法人日本薬学会の論文
• 1985-06-25

著者

• 板谷 泰助

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 渡辺 朝子

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 板谷 泰助

  金沢大学薬学部

• 松本 浩郎

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 原田 恒博

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 松本 浩郎

  Central Research Institute, Nissan Chemical Ind. Ltd.

• 松本 浩郎

  Central Research Institute Nissan Chemical Ind. Ltd.

• 原田 恒博

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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