構造に混乱のあるKinamycin類の化学

• 熊本 卓哉

  千葉大学大学院薬学研究院

• 石川 勉

  千葉大学大学院薬学研究院

• 大村 智

  (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

書誌事項

タイトル別名

• Chemistry of Structurally Confused Kinamycins
• コウゾウ ニ コンラン ノ アル Kinamycinルイ ノ カガク

抄録

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.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 62 (1), 49-58, 2004

  公益社団法人 有機合成化学協会

キーワード

• kinamycins
• antibiotics
• benzo [b] carbazole
• N-cyanamide
• prekinamycin
• benzo [b] fluorene
• diazoalkane
• isoprekinamycin
• structural determination
• synthetic studies

詳細情報

• CRID: 1390282680287714560
• NII論文ID: 10011952460
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.62.49
• COI: 1:CAS:528:DC%2BD2cXmtlWjsA%3D%3D
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 6824630
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I6824630
• データソース種別:
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  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可