Studies on the Synthesis of Compounds related to Adenosine 3', 5'-Cyclic Phosphate. IV. The Synthesis of 2-Sulfo- and 2-Carboxy-adenosine 3', 5'-Cyclic Phosphate
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概要
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The reactions of 2-mercapto-1,N^6-etheno c-AMP (c-AMP : adenosine 3', 5'-cyclic phosphate) (V) and 2-mercapto c-AMP (III) with hydrogen peroxide afforded 2-sulfo-1,N^6-etheno c-AMP (VIII) and 2-sulfo c-AMP (IX), respectively. Deblocking of the etheno residue of VIII afforded IX. Potassium cyanide reacted with 2-bromo-1,N^6-etheno c-AMP (VI) in dimethylformamide (DMF) at room temperature to yield 2-cyano-1,N^6-etheno c-AMP (X), which was isolated by Dowex 50-X8 (H^+) column chromatography. Compound (X) was hydrolyzed to 2-carbamoyl-1,N^6-etheno c-AMP (XI), then to 2-carboxy-1,N^6-etheno c-AMP (XII) by aqueous sodium hydroxide. Compound XII was converted to 1,N^6-etheno c-AMP (IV) by heating in dimethylsulfoxide (DMSO). Deblocking of the etheno residue of XI and XII afforded 2-carbamoyl c-AMP (XIII) and 2-carboxy c-AMP (XIV), respectively. Compound XIII was hydrolyzed by aqueous sodium hydroxide to yield XIV.
- 公益社団法人日本薬学会の論文
- 1980-01-25
著者
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加藤 元彦
Research And Development Division Kikkoman Corporation
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山次 信幸
Research and Development Division, Kikkoman Corporation
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加藤 元彦
Central Research Laboratories of Kikkoman Shoyu Co., Ltd.
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山次 信幸
Central Research Laboratories of Kikkoman Shoyu Co., Ltd.
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田原 恭子
Research Laboratory of Seishin Pharmaceutical Co., Ltd.
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田原 恭子
Research Laboratory Of Seishin Pharmaceutical Co. Ltd.
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山次 信幸
Research And Development Division Kikkoman Corporation
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