Syntheses of cyclic decapeptides with four ornithyl residues related to gramicidin S.
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概要
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Three cyclic decapeptides with four L-ornithyl residues related to gramicidin S (GS), <I>cyclo</I>(–Orn–Leu–Orn–D-Phe–Pro–)<SUB>2</SUB> (<B>D</B>-<B>L</B>-<B>12</B>), <I>cyclo</I>(–Orn–Leu–Orn–Phe–Pro–)<SUB>2</SUB> (<B>L</B>-<B>L</B>-<B>12</B>), and <I>cyclo</I>(–Orn–Leu–Orn–Phe–D-Pro–)<SUB>2</SUB> (<B>L</B>-<B>D</B>-<B>12</B>), were synthesized to investigate the contribution of increase of the basic amino acid residues and of configurations of phenylalanyl and prolyl residues toward antibacterial activity. These GS-like analogs were synthesized by the solution method of peptide synthesis. Protected cyclic decapeptides were synthesized through a cyclization reaction of linear decapeptide azide in pyridine. Hydrogenolysis of the protected cyclic decapeptides afforded crystalline tetrahydrochlorides of the desired analogs. In the experiment of circular dichroism, <B>D</B>-<B>L</B>-<B>12</B> gave a curve similar to that of GS, while <B>L</B>-<B>L</B>-<B>12</B> and <B>L</B>-<B>D</B>-<B>12</B> gave different curves. Antibacterial assays showed <B>L</B>-<B>L</B>-<B>12</B> exhibited substantial activities against Gram-negative bacteria, whereas <B>D</B>-<B>L</B>-<B>12</B> and <B>L</B>-<B>D</B>-<B>12</B> negligible activity.
- 公益社団法人 日本化学会の論文
著者
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Ando Setsuko
Department Of Chemistry Faculty Of Science Fukuoka University
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Takiguchi Hideo
Department Of Chemistry Faculty Of Science Fukuoka University
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Nishikawa Hiroshi
Department Of Chemistry Faculty Of Science Fukuoka University
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Izumiya Nobuo
Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University
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Izumiya Nobuo
Laboratory of Chemistry, Kurume Institute of Technology
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