New Neplanocin Analogues. IX. A Practical Preparation of (6'R)-6'-C-Methylneplanocin A (RMNPA), a Potent Antiviral Agent, and the Determination of Its 6'-Configuration. Diastereoselective Deamination by Adenosine Deaminase
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概要
- 論文の詳細を見る
We previously synthesized (6'R)- and (6'S)-6'-C-methylneplanocin A's (2a and 2b, respectively), and found that one of them has a potent antiviral activity, though its 6'-configuration has not been confirmed. This report describes the determination of the 6'-configuration and practical preparation of the antivirally active diastereomer. The 6'-configuration of the active diastereomer was determined as R by the modified Mosher's method as well as by synthesizing 2b from the known cyclopentenone derivative 10. A practical method for preparing the 6'R-diastereomer was developed by using diastereoselective deamination with Ado deaminase as the key step. Treatment of the diastereomeric mixture of 2a and 2b, which was prepared via an addition reaction of Me_3Al with the 6'-formyl derivative 3,with Ado deaminase from calf intestine, deaminated 2b selectively to give the corresponding (6'S)-inosine congener 5,and left the desired 2a not deaminated. After silica gel column chromatography, 2a was obtained in a pure form.
- 社団法人日本薬学会の論文
- 1997-01-15
著者
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Yaginuma S
Asahi Chemical Ind.co. Ltd. Shizuoka Jpn
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Yaginuma Satoshi
Institute For Life Science Research Asahi Chemical Industry Co. Ltd.
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Shuto S
Graduate School Of Pharmaceutical Sciences Hokkaido University
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MATSUDA Akira
Faculty of Pharmaceutical Sciences, Hokkaido University
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Matsuda A
Graduate School Of Pharmaceutical Sciences Hokkaido University
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Matsuda A
Faculty Of Pharmaceutical Sciences Hokkaido University
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SHUTO Satoshi
Faculty of Pharmaceutical Sciences, Hokkaido University
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OBARA Takumi
Institute for Life Science Research, Asahi Chemical Industry Co., Ltd.,
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Obata Tohru
Department Of Experimental Therapeutics Cancer Research Institute Kanazawa University
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Obara Takumi
Department Of Experimental Therapeutics Cancer Research Institute Kanazawa University
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Matsuda Akira
Department Of Pharmaceutical Sciences Faculty Of Pharmaceutical Sciences
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Matsuda A
Hokkaido Univ. Sapporo
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Matsuda Akira
The Department Of Internal Medicine Kin-ikyo Chuo Hospital
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Obata Takaaki
Department Of Experimental Therapeutics Cancer Research Institute Kanazawa University
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Matsuda Akira
Faculty Of Pharmaceutical Sciences Hokkaido University
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Yaginuma S
Asahi Chemical Ind. Co. Ltd. Shizuoka Jpn
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Yaginuma S
Institute For Life Science Research Asahi Chemical Industry Co. Ltd.
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