Chemistry of Structurally Confused Kinamycins

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  • Kumamoto Takuya
    Graduate School of Pharmaceutical Sciences, Chiba University
  • Ishikawa Tsutomu
    Graduate School of Pharmaceutical Sciences, Chiba University
  • Omura Satoshi
    (社)北里研究所 北里大北里生命科学研究所 北里大大学院感染制御科学府

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  • 構造に混乱のあるKinamycin類の化学
  • コウゾウ ニ コンラン ノ アル Kinamycinルイ ノ カガク

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Abstract

Kinamycin antibiotics, strongly active against gram-positive bacteria, were isolated from the culture broth of Streptomyces murayamaensis. Their structures were firstly determined to be a benzo [b] carbazoloquinone skeleton with N-cyanamide [N-C≡N] moiety. After that, prekinamycin was isolated from the same organism as a biosynthetic precursor and the same 6-6-5-6 ring system was also proposed for the structure. But problems still remained on the determination of substituent pattern at N-cyanamide moiety by spectroscopic means. Recently, the structures of kinamycins and prekinamycin were revised to be a benzo [b] fluorene skeleton with diazoalkane moiety [C--N+≡N]. However, a synthetic compound with the revised structure for prekinamycin was found to be different from natural prekinamycin, instead an isomeric benzo [a] fluorene skeleton, a 6-5-6-6 ring system was proposed for the natural product, which was newly named as isoprekinamycin. Herein the chemistry of kinamycins and their related compounds with structural confusions is reviewed, especially focused on the history of structural determination and recent synthetic studies.

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