わらびの究極発癌物質の合成およびDNAとの反応

• 山田 静之

  名古屋大学理学部化学科

• 木越 英夫

  名古屋大学理学部化学科

書誌事項

タイトル別名

• Synthesis of the Bracken Ultimate Carcinogen and Its Reactivity toward DNA
• ワラビ ノ キュウキョク ハツガン ブッシツ ノ ゴウセイ オヨビ DNA ト

抄録

Synthetic studies on the bracken ultimate carcinogen (3) and its artificial analogues (32, 33) are described. The synthesis of (-) -ptaquilosin (2) the aglycon of a potent carcinogen ptaquiloside (1) from bracken and its (+) - enantiomer (ent- 2) was achieved starting with (+) -dimenthyl (1R, 2R) -cyclopentane-1, 2-dicarboxylate. Dehydration of ptaquilosin (2) under weakly basic conditions led to the ultimate carcinogen (3). DNA cleaving activities of both enantiomers (3) were compared, the one (3) derived from natural (-) -ptaquilosin (2) being more efficient. Reactivities of the ultimate carcinogen (3) toward DNA are described. DNA was shown to be alkylated at the particular sites of purine bases and to undergo cleavage. The molecular mechanism of DNA cleavage with the ultimate carcinogen (3) was disclosed using deoxytetranucleotide d (GTAC) as a model DNA substrate.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 53 (1), 13-21, 1995

  公益社団法人 有機合成化学協会

キーワード

• Bracken
• Ptaquiloside
• Ultimate carcinogen
• Total synthesis
• Alkylation of DNA
• Molecular mechanism of DNA cleavage

詳細情報

• CRID: 1390001205310805504
• NII論文ID: 10001711642
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.53.13
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 3600473
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I3600473
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