1995 Fiscal Year Final Research Report Summary
Structural and Synthetic studies of biologically active natural glycoconjugates and peptides
| Project/Area Number |
05403035
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| Research Category |
Grant-in-Aid for General Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Research Field |
Bioorganic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
KUSUMOTO Shoichi Osaka Univ., Fac.of Sci.Professor, 理学部, 教授 (30028253)
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| Co-Investigator(Kenkyū-buntansha) |
FUKASE Koichi Osaka Univ., Fac.of Sci.Research Associate, 理学部, 助手 (80192722)
SUDA Yasuo Osaka Univ., Fac.of Sci.Assoc.Professor, 理学部, 助教授 (70179282)
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| Project Period (FY) |
1993 – 1995
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| Keywords | Glycoconjugates / Lipoteichoic acid / Heparin / Immunostimulation / Structural analysis / Synthesis / Fluorescence labeling / Phosphopeptides |
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| Research Abstract |
Structural and synthetic studies were performed on biologically active glycoconjugates and phosphopeptides for the purpose to elucidate the active structures responsible to their functions and the mechanisms of their action. Cytokine-inducing components were isolated and studied for their chemical structures from the lipoteichoic acid fraction of gram positive enterococcal cells through a multistep chromatographic procedure. The active components proved to be novel glycoconjugates different from lipopolysaccharides or muramyl peptides which are typical known immunostimulants of bacterial origin. Another high molecular glycoconjugate with similar biological functions from mycobacterial cells was also investigated.
Stereoselective construction of glycosidic linkages is an essential issue for chemical synthesis of complex glycoconjugates. Several efficient methods for this purpose were established by selective activation of thioglycosides. Some of the procedures were applied effectively to
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our synthetic work on endotoxic glycoconjugates. A novel procedure for elucidation of functional role of carbohydrates was also presented by preparation of bifunctional fluorescent reagents based on the known pyridylamination procedure. Labeled carbohydrates with these reagents are suitable for purification with HPLC and can then be coupled with high molecular matrices to form neo-glycoconjugates, which offers new route for biological investigation.
Chemical synthesis of a specific sulfated disaccharide corresponding to a partial structure of sulfated polysaccharide, heparin. Biological study with the synthetic specimen led to the conclusion that the particular disaccharide component plays an important role in platelet binding of heparin.
Synthetic study of phosphopeptide is important for basic understanding of the role of protein phosphorylation which is now known to be a crucial process in living systems. Reaction conditions as well as combination of protecting groups and coupling reagents were investigated for the preparation of phosphoserine containing peptides to establish efficient procedures applicable to both solid and liquid phase synthesis. Less
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