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)

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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.
天然有機化合物討論会の論文
1997-07-20

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)

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