ハナヤナギの成分研究-8-Domoic Acidの構造論-1- Studies on the Constituents of Chondria armata. VIII. : On the Structure of Domoic Acid. (1)

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The NMR spectrum of domoic acid (in CF_3COOH) indicates signals for a methyl at 1.43 p.p.m. (d;J=6.6 c.p.s.) and at 1.94 p.p.m. (a broad singlet), and no signal for an ethyl group. The methyl signal at 1.94 p.p.m. shows a long-range I-I coupling due to spin decoupling. The NMR spectrum of trimethyl domoate (in CDCl_3) shows a doublet methyl (J=7.0 c.p.s.) at 1.29 p.p.m., a methyl signal which indicates an allylic coupling at 1.79 p.p.m., and an olefinic proton signal corresponding to 3H at 5.5〜6.6 p.p.m. From its first-order analysis, the configuration of the 1,3-hexadienyl side chain was determined as trans : trans : S-trans. The infrared spectra of both domoic acid and trimethyl domoate show absorption due to the trans-double bond. The NMR spectrum of tetrahydrodomoic acid (in CF_3COOH) shows signals for a methyl bonded to a secondary carbon at 1.12 p.p.m. (d;J=6.0 c.p.s.) and at 1.22 p.p.m. (d;J=6.6 c.p.s.). It was concluded from these observations that the structure of domoic acid would be more appropriately represented as L_s-arabo-2-carboxy-4-(1-methyl-5-carboxy-trans : trans : S-trans-1,3-hexadienyl)-3-pyrrolidineacetic acid (VIII) rather than the previously proposed L_s-arabo-2-carboxy-4-(1-methyl-2-carboxy-1,3-hexadieny1)-3-pyrrolidineacetic acid (I).

収録刊行物

  • 薬学雑誌

    薬学雑誌 86(10), 874-877, 1966-10

    公益社団法人日本薬学会

各種コード

  • NII論文ID(NAID)
    110003653083
  • NII書誌ID(NCID)
    AN00284903
  • 本文言語コード
    JPN
  • ISSN
    00316903
  • NDL 記事登録ID
    8461832
  • NDL 雑誌分類
    ZS51(科学技術--薬学)
  • NDL 請求記号
    Z19-411
  • データ提供元
    NDL  NII-ELS 
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