Chemical transformation of seldomycin 5 into 3'-deoxyseldomycin 5 and related compounds.

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概要

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• 3′-Deoxyseldomycin 5 (<B>2</B>), 2′-deamino-3′-epiamino-3′-deoxyseldomycin 5 (<B>14</B>), and 2′,3′-epimino-2′-deamino-3′-deoxyseldomycin 5 (<B>15</B>) were prepared from seldomycin 5 (<B>1</B>). Treatment of hexa-<I>N</I>-ethoxycarbonyl (ecb)-3′-<I>O</I>-tosylseldomycin 5 with sodium borohydride in DMSO gave the corresponding <I>N</I>-ecb-derivatives of <B>2</B>, <B>14</B>, and <B>15</B>. Removal of the ecb groups of these compounds with aq potassium hydroxide gave the free bases <B>2</B>, <B>14</B>, and <B>15</B>, respectively. Structure determination of the products was performed by means of MS, CMR, PMR, and chemical reactions. It was found that <B>2</B> exhibits a more potent and broader antibacterial activity than the parent compound <B>1</B>, and <B>14</B> shows unique antibacterial spectrum against resistant strains, whereas <B>15</B> has almost no activity.

• 公益社団法人 日本化学会の論文

著者

• Matsushima Hideo

  Tokyo Research Laboratory, Kyowa Hakko Kogyo Co.

• Matsushima Hideo

  Tokyo Research Laboratory, Kyowa Hakko

• Kitaura Kozo

  Pharmaceuticals Research Laboratory, Kyowa Hakko

• Mori Yasuki

  Tokyo Research Laboratory, Kyowa Hakko

関連論文

• Chemical transformation of seldomycin 5 into 3'-episeldomycin 5 and its antibacterial activity.
• Chemical transformation of seldomycin 5 into 3'-deoxyseldomycin 5 and related compounds.
• Preparation of fortamine and 6-epi-purpurosamine B from fortimicin B.

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