Relative and Absolute Configuration of Antitumor Agent SW-163D
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概要
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Our interest on engineering non-ribosomal synthetase responsible for SW-163 biosynthesis prompted us to determine the relative and absolute configuration of antitumor cyclic depsipeptide SW-163s. We first isolated and identified SW-163 homologs D, F and G as known compounds UK-63598, UK-65662 and UK-63052, respectively. Both enantiomers of the unusual constitutive amino acid, N-methylnorcoromic acid, were synthesized in chiral forms starting from (R)- and (S)-1,2-propanediol. The hydrolyzate of SW-163D, a major constituent of this family, was converted with Marfey’s reagent, 1-fluoro-2,4-dinitrophenyl-5-L-alanine-amide (L-FDAA), and the resulting mixture of amino acid derivatives was subjected to an LC/MS analysis. Compared with authentic samples, the analytical data unambiguously show that SW-163D consisted of L-Ala, D-Ser and (1S, 2S)-N-methylnorcoronamic acid. The remaining stereochemistry of the N-methylcysteine moieties was determined from NOE data.
- 社団法人 日本農芸化学会の論文
- 2007-12-23
著者
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WATANABE Kenji
Department of Kampo Medicine, Keio University, School of Medicine
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Oikawa Hideaki
Div. Of Chemistry Graduate School Of Sci. Hokkaido Univ.
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Oikawa Hideaki
Division Of Applied Bioscience Graduate School Of Agriculture Hokkaido University
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TAKAHASHI Kosaku
Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University
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FUKUSHI Eri
Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University
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OGURI Hiroki
Division of Chemistry, Graduate School of Science, Hokkaido University
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NAKAYA Mino
Division of Chemistry, Graduate School of Science, Hokkaido University
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Fukushi Eri
Division Of Applied Bioscience Graduate School Of Agriculture Hokkaido University
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Takahashi Kosaku
Division Of Applied Bioscience Graduate School Of Agriculture Hokkaido University
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Watanabe Kenji
Department Of Gastroenterology Osaka City University Graduate School Of Medicine
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Nakaya Mino
Division Of Chemistry Graduate School Of Science Hokkaido University
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Oguri Hiroki
Division Of Chemistry Graduate School Of Science Hokkaido University
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Watanabe Kenji
Department Of Gastroenterology Graduate School Of Medicine Osaka City University
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Watanabe Kenji
Department Of Anatomy Fukui Medical School
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Watanabe Kenji
Division Of Chemistry Graduate School Of Science Hokkaido University
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Watanabe Kenji
Department Of Agricultural Chemistry College Of Agriculture And Veterinary Medicine Nihon University
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Watanabe Kenji
School Of Pharmaceutical Sciences University Of Shizuoka
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