A Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues.

DOI DOI PDF Web Site 被引用文献11件 参考文献33件
  • Liu Wen-Chi
    Department of Chemistry, Graduate School of Science, Osaka University
  • Oikawa Masato
    Department of Chemistry, Graduate School of Science, Osaka University
  • Fukase Koichi
    Department of Chemistry, Graduate School of Science, Osaka University
  • Suda Yasuo
    Department of Chemistry, Graduate School of Science, Osaka University
  • Kusumoto Shoichi
    Department of Chemistry, Graduate School of Science, Osaka University

書誌事項

タイトル別名
  • Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues
公開日
1999
DOI
  • 10.1246/bcsj.72.1377
  • 10.1002/chin.199949198
公開者
公益社団法人 日本化学会

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説明

Lipid A and its two chemically stable analogues, wherein the glycosidic phosphoryl groups in lipid A is replaced with 2-(phosphonooxy)ethyl or carboxymethyl groups, have been synthesized by an improved and divergent route via a common allyl glycoside intermediate in which the 4-hydroxy group was protected as a benzyl ether. The total yields were more than 20% for 11 or 12 steps starting from allyl 4,6-O-benzylidene-2-deoxy-2-(trichloroethoxycarbonylamino)-D-glucopyranoside. These synthetic chemically stable analogues induce interleukin-6 and tumor necrosis factor α in human peripheral whole blood cells with potencies comparable to those by natural-type synthetic lipid A. The Limulus activities of both analogues were found to be even stronger than the activity of the natural-type one.

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