糖鎖分析法の開発とその生理活性糖タンパク質糖鎖構造解析への応用
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I developed novel analytical methods of Asn-linked neutral- and sialyloligosaccharides,and O-linked oligosaccharides derived from glycoprotein swith use of high performance liquid chromatography ; (HPLC). The oligosaccharides were labeled with a ultra-violet absorbing compound, p-aminobenzoic ethyl ester (ABEE), by reductive animation to obtain high sensitivity of detection and sufficient resolution on HPLC. The ABEE derivatives of the neutral oligosaccharides can be efficiently separated by a combination of normal-phase and reversed-phase HPLC and the anionic oligosaccharides by a combination of anion-exchange and reversed-phase HPLC. These methods have been successfully adapted for the analysis of the oligosaccharides from some bioactive glycoproteins. I) A sea squirt H-antigen was found to contain the following allergenically active O-linked oligosaccharides: GalNAc β1-4 (GalNAc α1-2 Fuc α1-3) GlcNAc β1-3GalNAc-ol, GalNAc β1-4GlcNAc β1-3 (GalNAc β 1-4 GlcNAc β1-6) GalNAc-ol, GalNAc β1-4 (±Fuc α1-3) GlcNAc β1-3[GalNAc β1-4 (Fuc α1-3) GlcNAc β1-6]GalNAc-ol, and GalNAcβ1-4 (GalNAc α1-2Fuc α1-3) GlcNAc β1-3[GalNAc β1-4 (GalNAc α1-2Fuc α1-3) GlcNAc β1-6]GalN Ac-ol. Disaccharide units GalNAcα1-2Fucα1-, and GalNAc β1-4GlcNAc β1- are considered to be the allergenically-specific epitopes in this sea squirt asthmatic allergy. II) Hen egg-yolk immunoglobulin was found to contain three types of Asn-linked oligosaccharides; monoglucosylated oligomannose type oligosaccharides with structures of Glcα1-3Man_<7-9>GlcNAc-GlcNAc, a series of oligomannose oligosaccharides, Man_<5-9>GlcNAc-GlcNAc, and biantennary complex type oligosaccharides with the core structures Manα1-6 (Manα1-3)(±GlcNAc β1-4)Man β1-4GlcNAc β1-4(±Fucα1-6) GlcNAc. The strucrutal feature of the oligosaccharides was quite different from that of mammalian immunoglobulin. The glucosylated oligoaccharides, Glc_1-Man_<7-6> GlcNAc_2, have not previously been reported in mature glycoproteins from any source. III) Predominant oligosaccharides accumulated in the kidney of a calf with β-mannosidosis were found to be Manβ1-4GlcNAc and Man β1-4GlcNAc β1-4GlcNAc. As expected in a β-mannosidase deficiency state, the terminal residue of the accumulated oligosaccharides was a β-linked mannose. The structures of the accumulating oligosaccharides were identical to those accumulated in caprine β-mannosidosis tissues.
- 福山大学の論文
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