Studies of peptide antibiotics. XXXVIII. Synthesis of S,S'-bi([1-L-hemicystine]-gramicidin S), a dimerized analog of gramicidin S.

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概要

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• To investigate the importance of the orientation of side chains of amino acid residues in gramicidin S (GS) for the antibacterial activity, a dimerized analog of GS, namely <I>S</I>,<I>S</I>′-bi([1-L-hemicystine]-GS) (<B>13</B>) was synthesized <I>via</I> removal of <I>p</I>-methoxybenzyl group of [1-<I>S</I>-<I>p</I>-methoxybenzyl-L-cysteine]-GS (<B>12</B>) and subsequent oxidation. Compound <B>12</B> showed the same antibacterial activity as GS, whereas <B>13</B> was inactive. The resemblance of ORD curves of the two analogs to that of GS suggested the similarity of peptide-backbone structure of these three compounds. Strong activity of <B>12</B> was explained by similar conformation of <B>12</B> to that of GS. To explain the inactivity of <B>13</B>, a molecular model was proposed; four hydrophilic side chains are located on surface of the molecule, whereas six hydrophobic are burried.

• 公益社団法人 日本化学会の論文

著者

• Aoyagi Haruhiko

  Laboratory Of Biochemistry Faculty Of Science Kyushu University

• Izumiya Nobuo

  Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University

• Ueda Kazuo

  Laboratory Of Environmental Development Engineering College Of Agriculture

• Izumiya Nobuo

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

• Sato Kazuki

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

• Kondo Michio

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

• Ueda Kazuo

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

• Aoyagi Haruhiko

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

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