Synthesis of 6-Thioguanine and 2,6-Diaminopurine Nucleosides and Nucleotides from Adenine Counterparts via a Facile Rearrangement in the Base Portion (Nucleosides and Nucleotides. XIX)

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概要

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• A method of conversion of an adenine moiety to 6-thioguanine (and guanine) and 2,6-diaminopurine moiety in the nucleoside and nucleotide levels were presented. The action of cyanogen bromide with adenosine N^1-oxide afforded an 1,2,4-oxadiazolo (3,2-f)-purine riboside (2a), which was in a pH dependent equilibrium with N^6-cyanoadenosine N^1-oxide (3a). Methylation followed by alkaline treatment of 3a resulted in a rearrangement leading to give 2-amino-N^6-methoxyadenosine (5a). Catalytic hydrogenation of 5a gave 2,6-diaminopurine riboside (6a). Sulfhydrolysis of 5a gave 6-thioguanosine (7a). By a similar reaction sequence 2'-deoxyadenosine was converted to 2'-deoxy-6-thioguanosine (7b) and 2,6-diaminopurine 2'-deoxyriboside, respectively. Starting from the N^1-oxides of adenosine 5'-phosphate (AMP), 2'-deoxyadenosine 5'-phosphate (dAMP) and 9-β-D-arabinofuranosyladenine 5'-phosphate (araAMP), the corresponding 6-thioguanine nucleotides were likewise prepared.

• 公益社団法人日本薬学会の論文
• 1978-07-25

著者

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 三浦 一伸

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 上田 亨

  北海道大学薬学部

• 三浦 一伸

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 笠井 嗣夫

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 笠井 嗣夫

  Faculty Of Pharmaceutical Sciences Hokkaido University

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