1990 Fiscal Year Final Research Report Summary
Chemical Study on Immunostimulating Natural Glycoconjugates
| Project/Area Number |
01470028
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
天然物有機化学
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| Research Institution | Osaka University |
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Principal Investigator |
KUSUMOTO Shoichi Osaka University, Department of Chemistry Professor, 理学部, 教授 (30028253)
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| Co-Investigator(Kenkyū-buntansha) |
FUKASE Koichi Osaka University, Department of Chemistry Research Assistant, 理学部, 助手 (80192722)
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| Project Period (FY) |
1989 – 1990
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| Keywords | Immunostimulation / Glnoーconjugates / lipoteichoic Acid / LipopoLy Saccharides / リポ多糖 |
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| Research Abstract |
Synthetic and structural studies were performed on amphiphilic glycoconjugates from bacterial cell surfaces in order to study the respective chemical entities responsible for their characteristic immunostimulating and antitumor activities.
Lipoteichoic Acid (LTA) of Staphylococcus pyogenes was the first target of our synthesis because of the recently described antitumor activity of this particular LTA. According to the proposed structure, the poly (glycerol phosphate) and the glycolipid part were synthesized separately and then coupled together to form the desired basic structure of the LTA. The optically pure glycerol phosphate part was synthesized by a novel efficient procedure from chirally protected glycerol components, which were prepared from D-mannitol. The phophodiesters between glycerols were formed by the phosphoroamidite procedure. For the formation of the glycolipid, novel and versatile methods for selective protection of hydroxyl groups were exploited by means of p-nitro-and p-pivaloylaminobenzyl groups. After the complete deprotection, the synthetic LTA and its partial structures are being subjected to biological tests.
A novel immunostimulating glycoconjugate recently found in BCG cells were effectively purified by gel filtration and partition chromatography and shown to be a new-type of lipopolysaccharide different from that of gram-negative bacteria. A similar compound was also isolated from cells of Mycobacterium bovis ravenel.
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