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Structures of asparagine-linked oligosaccharides from hen egg-yolk antibody (IgY). Occurrence of unusual glucosylated oligo-mannose type oligosaccharides in a mature glycoprotein

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Abstract

Asparagine-linked oligosaccharides present on hen egg-yolk immunoglobulin, termed IgY, were liberated from the protein by hydrazinolysis. AfterN-acetylation, the oligosaccharides were labelled with a UV-absorbing compound,p-aminobenzoic acid ethyl ester (ABEE). The ABEE-derivatized oligosaccharides were fractionated by anion exchange, normal phase and reversed phase HPLC, and their structures were determined by a combination of sugar composition analysis, methylation analysis, negative ion FAB-MS, 500 MHz1H-NMR and sequential exoglycosidase digestions. IgY contained monoglucosylated oligomannose type oligosaccharides with structures of Glcα1-3Man7–9-GlcNAc-GlcNAc, oligomannose type oligosaccharides with the size range of Man5–9GlcNAc-GlcNAc, and biantennary complex type oligosaccharides with core region structure of Manα1-6(±GlcNAcβ1-4)(Manα1-3)Manβ1-4GlcNAcβ1-4(±Fucα1-6)GlcNAc. The glucosylated oligosaccharides, Glc1Man8GlcNAc2 and Glc1Man7GlcNAc2, have not previously been reported in mature glycoproteins from any source.

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Abbreviations

IgG, IgM, IgD, IgE, and IgA:

immunoglobulin G, M, D, E, and A, respectively

IgY:

egg-yolk antibody

ABEE:

p-aminobenzoic acid ethyl ester

HPLC:

high performance liquid chromatography

FAB-MS:

fast atom bombardment mass spectrometry

Hex:

hexose

HexNAc:

N-acetylhexosamine

hCG:

human chorionic gonadotropsin

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Authors and Affiliations

  1. Department of Biotechnology, Faculty of Engineering, Fukuyama University, 729-02, Fukuyama, Hiroshima, Japan

    Masaya Ohta, Satoru Yamamoto, Takehiko Yamamoto & Fumito Matsuura

  2. Division of Biomedical Polymer Science, Institute for Comprehensive Medical Science, Fujita Health University School of Medicine, 470-11, Toyoake, Aichi, Japan

    Jiharu Hamako & Tsuguo Mizuochi

  3. Central Research Laboratories, Taiyo Kagaku Co. Ltd., 510, Yokkaichi, Mie, Japan

    Hajime Hatta & Mujo Kim

  4. Department of Fermentation Technology, Faculty of Engineering, Hiroshima University, 724, Higashi-Hiroshima, Hiroshima, Japan

    Satoru Oka

Authors
  1. Masaya Ohta
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  2. Jiharu Hamako
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Ohta, M., Hamako, J., Yamamoto, S. et al. Structures of asparagine-linked oligosaccharides from hen egg-yolk antibody (IgY). Occurrence of unusual glucosylated oligo-mannose type oligosaccharides in a mature glycoprotein. Glycoconjugate J 8, 400–413 (1991). https://doi.org/10.1007/BF00731292

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  • DOI: https://doi.org/10.1007/BF00731292

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