Synthesis and Biological Activities of Lipid A Analogs Possessing <i>β</i>-Glycosidic Linkage at 1-Position

DOI DOI PDF 被引用文献4件 参考文献30件
  • Fukase Koichi
    Department of Chemistry, Graduate School of Science, Osaka University
  • Ueno Atsushi
    Department of Chemistry, Graduate School of Science, Osaka University
  • Fukase Yoshiyuki
    Department of Chemistry, Graduate School of Science, Osaka University
  • Oikawa Masato
    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
  • Synthesis and Biological Activities of Lipid A Analogs Possessing .BETA.-Glycosidic Linkage at 1-Position.
  • Synthesis and Biological Activities of Lipid A Analogues Possessing β‐Glycosidic Linkage at 1‐Position.
  • Synthesis and biological activities of lipid A analogs possessing β-glycosidic linkage at 1-position
公開日
2003
DOI
  • 10.1246/bcsj.76.485
  • 10.1002/chin.200322216
公開者
公益社団法人 日本化学会

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説明

New lipid A analogs having acidic groups β-glycosidically linked at the 1-position were synthesized in order to investigate the structural requirement for immunostimulating and endotoxic activity of lipid A. The β-(phosphonoxy)ethyl (PE) and carboxymethyl (CM) analogs of Escherichia coli type having six acyl groups and those of the biosynthetic precursor type having four acyl groups were synthesized via a divergent synthetic route. The E. coli type β-(phosphonoxy)ethyl analog, which was previously reported to be not endotoxic, showed strong immunostimulating activity comparable to the natural-type α-analog. The acidic functional groups are concluded to be essential but their strict spatial arrangement is not required for expression of the biological activity.

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