68(P46) 標識化したリピドA関連化合物の合成研究(ポスター発表の部)

DOI

書誌事項

タイトル別名
  • 68(P46) Synthetic Study of ^3H-, ^<13>C-, and Fluorescence-labeled Lipid A Analogues

抄録

Lipopolysaccharide (LPS) is a component of cell surface architecture of Gram-negative bacteria. It exhibits both toxic and beneficial bioactivities for higher animals. The actual bioactive principle of LPS is glycolipid called lipid A (1) which is the partial structure present at the reducing end of LPS. It is also known that the biosynthetic precursor 2 of lipid A inhibits the bioactivity of LPS and lipid A (1). Although an interaction between lipid A portion of LPS and certain receptor on macrophage cell is expected to play an important role for bioactivities, the identification of the receptor and their binding manner still remain to be studied. So we planned to synthesize ^3H-, ^<13>C-, and fluorescence-labeled lipid A analogues, which will be useful for the binding study, in different synthetic pathways. Allyl-type protecting groups were employed for the final protecting groups in the present synthetic study of fluorescence-labeled lipid A. The fluorescence (BODIPY^[○!R]) group was introduced to 6'-O-position of lipid A using glycine as a linker after the formation of disaccharide backbone (13→14). Radio-labeling was found to be effected on the ethylene glycol linker to the stable phosphonooxyethyl analogue of lipid A by NaB^3H_4 reduction at the final synthetic stage. 6-^<13>C-Labeled glucose (26) was used as the starting material for the synthesis of ^<13>C-labeled analogue. An efficient synthetic pathway toward suitably protected glucosamine 34 was developed via 1,6-anhydro-β-glucopyranose derivatives 28-32.

収録刊行物

詳細情報 詳細情報について

  • CRID
    1390001206079121280
  • NII論文ID
    110006679562
  • DOI
    10.24496/tennenyuki.39.0_403
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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