Synthesis of a peptide lactone, N-(3-hydroxypicolinyl)-threonyl-D-leucyl-prolylsarcosyl-leucyl-alanyl-alanine threonine lactone.
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概要
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The synthesis of a peptide lactone, <I>N</I>-(3-hydroxypicolinyl)-threonyl-D-leucyl-prolylsarcosyl-leucyl-alanyl-alanine Threonine Lactone (<B>21</B>) is described. The <I>t</I>-butoxycarbonyl group of <I>t</I>-butyl <I>O</I>-(<I>t</I>-butoxycarbonyl-alanyl)-<I>N</I>-benzyloxycarbonyl-threonyl-D-leucyl-prolylsarcosinate (<B>12</B>) was deblocked selectively with formic acid in good yield. The coupling of <B>12</B> with the azide derived from <I>t</I>-butoxycarbonyl-leucyl-alanine hydrazide (<B>15</B>) with isopentyl nitrite gave a heptapeptide ester <B>17</B>. Deblocking, cyclization, and hydrogenation gave a heptapeptide lactone <B>20</B> which was coupled with 3-hydroxypicolinic acid yielding <B>21</B>.
- 公益社団法人 日本化学会の論文
著者
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Kinoshita Hideki
Department Of Bioscience And Biotechnology Faculty Of Agriculture Shinshu University:united Graduate
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Kotake Hiroshi
Department of Chemistry, Faculty of Science, Kanazawa University
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