The Isomerization of Purine Nucleosides in a Dilute Alkaline Solution

スポンサーリンク

概要

• 論文の詳細を見る

• A further study of the isomerization of inosine (<B>1a</B>) in a dilute alkaline solution has revealed the formation of α-pyranbsyl isomer (<B>4a</B>) and its β-isomer (<B>3a</B>). Adenosine (<B>1b</B>) was isomerized at 130 °C for 12 hr at pH 10, giving α-furanosyl (<B>2b</B>) (2% yield), β-pyranosyl (<B>3b</B>) (11%), and the α-pyranosyl isomer (<B>4b</B>) (0.8%), respectively; 65% of the <B>1b</B> also remained. 9-β-D-Ribopyranosyl-6-mercaptopurine (<B>3c</B>) was prepared through this reaction from the corresponding β-furanoside (<B>1c</B>). Arabinosyl or xylosyl purine nucleosides were also isomerized, whereas neither 2′-deoxy nor 2′-substituted nucleoside showed any clear evidence of isomerization. In conclusion, the purine base and the 2′-hydroxyl anion are essential to the alkaline isomerization of nucleosides. By means of NMR, both <B>4a</B> and <B>4b</B> were found to have a 1C conformation, while <B>3a</B> and <B>3b</B> have a Cl conformation.

• 公益社団法人 日本化学会の論文

著者

• Suzuki Yoshihisa

  Central Research Laboratories, Ajinomoto Co., Inc.

• Yatabe Setsuko

  Central Research Laboratories, Ajinomoto Co., Inc.

関連論文

• Polymorphism of Inosine. III. The Equilibrium for the Inosine–Dimethyl Sulfoxide–Water System
• A Study of the Molecular Compound between Inosine and Tryptophan
• Some Properties of the Salt between Inosine and L-Lysine
• The Formation of Crystalline Complexes between Inosine and Several Hydroxybenzoic Acids
• The Formation of Crystalline Molecular Complexes between Inosine and Several Phenols
• The Isomerization of Purine Nucleosides in a Dilute Alkaline Solution

スポンサーリンク