Preparation, stereochemistry, and antibacterial activity of gramicidin S analogs containing N-methyl groups.
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概要
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The <I>N</I>-methylated analogs of gramicidin S, namely [Orn(Me<SUB>3</SUB><SUP>+</SUP>)<SUP>2,2′</SUP>]-, [MeOrn<SUP>2,2′</SUP>, D-MePhe<SUP>4,4′</SUP>]-, [MeOrn(Me)<SUP>2,2′</SUP>, D-MePhe<SUP>4,4′</SUP>]-, and [MeOrn(Me<SUB>3</SUB><SUP>+</SUP>)<SUP>2,2′</SUP>, D-MePhe<SUP>4,4′</SUP>]gramicidin S, were prepared by the use of quaternization reaction of free amino groups with CH<SUB>3</SUB>I–KHCO<SUB>3</SUB> in methanol and/or selective amide-methylation with CH<SUB>3</SUB>I–Ag<SUB>2</SUB>O in DMF. The conformations of these synthetic analogs were shown to be of β-sheet type similar to that of parent gramicidin S by <SUP>1</SUP>H NMR analysis and CD spectral comparison. The <I>N</I>-methyl group-containing analogs exhibited essentially the same antibacterial activity against Gram-positive bacteria as gramicidin S itself.
- 公益社団法人 日本化学会の論文
著者
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Butsugan Yasuo
Department Of Applied Chemistry Nagoya Institute Of Technology
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Saito Kazuki
Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences, University of Tokyo
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Fukuta Norihito
Department of Appliced Chemistry, Nagoya Institute of Technology
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Kawai Masao
Department of Appliced Chemistry, Nagoya Institute of Technology
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Ohya Masashi
Department of Appliced Chemistry, Nagoya Institute of Technology
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