Total Synthesis of Agrocin 84 and Phosmidosine as Naturally Occurring Nucleotidic Antibiotics Having P-N Bond Linkages
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概要
- 論文の詳細を見る
This review deals with our recent studies of the synthesis of naturally occurring nucleic acid derivatives having P-N linkages. The total synthesis of a nucleotidic antibiotic, agrocin 84 (1), having two different types of unique phosphoramidate bonds is described in detail. Synthesis of this natural product remained unrealized for a long time after its discovery in 1974, but development of a new method for the construction of the P-N bond led us to our final goal. Phosmidosine (2) is an antibiotic that has an antifungal activity and has a rare <I>O</I>-methylated phosphoramidate structure. This compound was also successfully synthesized by use of 5-(3, 5-dinitrophenyl)-1<I>H</I>-tetrazole (DNPT) as the powerful activator of an <I>N</I>-prolyl phosphorodiamidite derivative that was condensed with an 8-oxoadenosine derivative. Several related compounds were also synthesized. These phosmidosine derivatives were found to exhibit significant antitumor activities. In connection with these studies, the synthesis and biological properties of aminoacylamido-AMP derivatives having N-P bonds as stable analogues of aminoacyl-AMP are also described.
- 社団法人 有機合成化学協会の論文
- 2001-11-01
著者
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WADA Takeshi
Department of Interventional Neuroradiology, Ishinkai Yao General Hospital
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SEIO Kohji
Department of Life Science, Tokyo Institute of Technology
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SEKINE Mitsuo
Department of Life Science, Tokyo Institute of Technology
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Moriguchi Tomohisa
Department Of Life Science Tokyo Institute Of Technology
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Moriguchi Tomohisa
Department Of Chemistry And Chemical Biology Graduate School Of Engineering Gunma University
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Wada Takeshi
Department Of Medical Genome Sciencs Graduate School Of Frontier Sciences The University Of Tokyo
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Wada Takeshi
Department Of Interventional Neuroradiology Ishinkai Yao General Hospital
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Seio Kohji
Department Of Life Science Tokyo Institute Of Technology
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Sekine Mitsuo
Department Of Life Science Tokyo Institute Of Technology
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Sekine Mitsuo
Department Of Life Chemistry Tokyo Institute Of Technology
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Wada Takeshi
Department Of Life Science Tokyo Institute Of Technology
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Wada Takeshi
Department Of Electronics Faculty Of Engineering Kyoto University
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