Syntheses and properties of [1,1'-bis(.ALPHA.-aminoisobutyric acid)]gramicidin S and [1-.ALPHA.-aminoisobutyric acid]semigramicidin S.
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概要
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Analogs of gramicidin S, [1,1′-bis(α-aminoisobutyric acid)]gramicidin S (<B>18</B>) and [1-α-aminoisobutyric acid] semigramicidin S (<B>11</B>), have been synthesized by a conventional solution method. The cyclization reactions of a linear pentapeptide active ester and a linear decapeptide active ester yielded exclusively a protected cyclic pentapeptide and a protected cyclic decapeptide, respectively. After deprotection of these peptides, we obtained the final products (<B>11</B> and <B>18</B>). The mobility of <B>18</B> in paper electrophoresis was the same as that of gramicidin S, however, the CD spectrum of <B>18</B> in a methanol solution showed a markedly different pattern from that of gramicidin S. Both analogs (<B>11</B> and <B>18</B>) are inactive against the Gram-positive microorganisms tested. The results suggest that the positions of the valine residues in gramicidin S require a hydrophobic amino acid having L-configuration to show activity.
- 公益社団法人 日本化学会の論文
著者
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KONDO Michio
Department of Chemistry, Faculty of Science and Engineering, Saga University
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Sato Ken-ichi
Department Of Agricultural Chemistry The University Of Tokyo:(present Office)nihon Pall Ltd.
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Kondo Michio
Department Of Chemistry Faculty Of Science And Ehgineering Saga University
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Kimura Mikio
Department of Chemistry, Faculty of Science and Engineering, Saga University
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Horimoto Hideaki
Department of Chemistry, Faculty of Science and Engineering, Saga University
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