Synthesis of 1-N-Oxides of Adenosine and 2-Alkyladenosine and Inosine 1-N-Oxide 5'-Phosphate

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概要

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• Reaction of 5-amino-4-cyano-1-(2', 3'-O-isopropylidene-β-D-ribofuranosyl) imidazole (I) with ethyl orthoformate followed by treatment with hydroxylamine afforded 2', 3'-O-isopropylideneadenosine 1-N-oxide (IVa), from which adenosine 1-N-oxide (Va) was obtained by removal of the isopropylidene group. Similarly, 2-methyladenosine 1-N-oxide (Vb) and 2-ethyladenosine 1-N-oxide (Vc) were prepared. When O-methylhydroxylamine was substituted for hydroxylamine in the ring closure reaction of IIa, 9-(2', 3'-O-isopropylidene-β-D-ribofuranosyl)-6-methoxyaminopurine (VIII) was obtained by ring opening and subsequent recyclization of the 1-methoxyadenosine derivative (VII). Deamination of IVa with nitrous acid resulted in the formation of inosine 1-N-oxide (X). Its isopropylidene derivative (XI) was phosphorylated with phosphoryl chloride to give, after acidic treatment, inosine 1-N-oxide 5'-phosphate (XII), whose flavoring activity was examined.

• 公益社団法人日本薬学会の論文
• 1969-06-25

著者

• 山崎 晤弘

  Central Research Laboratories, Ajinomoto Co., Inc.

• 熊代 泉

  Central Research Laboratories, Ajinomoto Co., Inc.

• 熊代 泉

  Central Research Laboratories Ajinomoto Co. Inc.

• 山崎 晤弘

  Central Research Laboratories Ajinomoto Co. Inc.

• 竹西 忠男

  Central Research Laboratories, Ajinomoto Co., Inc.

• 竹西 忠男

  Central Research Laboratories Ajinomoto Co. Inc.

関連論文

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• A New Method for the Synthesis of 2'-Amino-2'-deoxyguanosine and -adenosine and Their Derivatives
• 221 プリンアラビノシド類の酵素的合成
• Phenylalanine Derivatives Enhancing Intestinal Absorption of Insulin in Mice
• Synthesis of 5-Amino-1-(3'-deoxy-β-D-ribofuranosyl)-4-imidazolethiocarboxamide
• Synthesis of 2'- and 3'-Deoxyinosines
• Synthesis of Thioinosine and Thio-AICA-riboside Analogs
• Synthesis of 9-β-D-Xylofuranosyl-6-mercaptopurine and 9-β-D-Xylofuranosylguanine 5'-Phosphate
• Synthesis of 9-(4'-Hydroxybutyl)-2-amino-6-hydroxypurine 4'-Phosphate
• Synthesis of 1-N-Oxides of Adenosine and 2-Alkyladenosine and Inosine 1-N-Oxide 5'-Phosphate
• Synthesis of Thio-AICA, 6-Thioxanthine, Isoguanine Analogs, and Their Ribosides
• Synthesis of Some N^1-Methyl-2-substituted Inosines and Their 5'-Phosphates
• Synthesis of 2-Alkylthioinosine 5'-Phosphates and N^2-Methylated Guanosine 5'-Phosphates
• Studies on Coenzyme Analogs. XIII. Oxidation of Methylmercaptopurine and its Nucleoside by means of N-Chloro-and N-bromosuccinimide.
• Potential Antimetabolites. IV. Synthesis of 2,6-Bis-alkylthiopurine Ribosides and their Selective Substitution by Nucleophilic Reagents.
• トランスグリコシレーション法によるプリンヌクレオシド類の合成

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