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1H-NMR spectroscopic characterization of dansyl glyco-asparagines derived from hen egg white clycoproteins

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Abstract

Dansyl glyco-asparagines were prepared from a partially fractionated mixture of hen egg white glycoproteins. Reverse-phase high performance liquid chromatography (HPLC) on a silica-based octadecyl column yielded ten such derivatives in a virtually pure state. The detailed structures of the glyco-asparagines were identified by 500-MHz1H nuclear magnetic resonance (NMR) spectroscopy. Two of them were found to be of the oligomannosideN-type, four were of the intersected-hybridN-type and another four were of the intersected multi-antennaryN-type. In monogalactosylated, intersected structures the galactose residue was proved by1H-NMR to be attached in β(1–4)-linkage to the GlcNAcβ1-4Manα1–3 branch.

Dansyl glyco-asparagines turned out to be suitable derivatives for1H-NMR spectroscopic analysis. The combination of HPLC and high-resolution NMR spectroscopy of such derivatives proved to be a powerful technique in studying the (micro-)heterogeneity of sugar chains in glycoproteins.

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Abbreviations

dns:

dansyl (5-dimethylaminonaphthalene-1-sulfonyl)

ODS:

octadecyl-silica

WEFT:

water-eliminating Fourier transform

DSS:

sodium 4,4-dimethyl-4-silapentane-1-sulfonate

OVA:

ovalbumin

OVM:

ovomucoid

OVT:

ovotransferrin

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Author notes

  1. Hitoo Iwase

    Present address: Department of Biochemistry, School of Medicine, Kitasato University, 1-15-1 Sagamihara, 228, Kanagawa, Japan

Authors and Affiliations

  1. Department of Bio-Organic Chemistry, University of Utrecht, Croesestraat 79, NL-3522 AD, Utrecht, The Netherlands

    Herman Van Halbeek & Johannes F G Vliegenthart

  2. Department of Biochemistry, Delta Regional Primate Research Center, Tulane University, 70112, New Orleans, Louisiana, USA

    Hitoo Iwase, Suchen Li & Yu-Teh Li

Authors
  1. Herman Van Halbeek
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  2. Johannes F G Vliegenthart
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  3. Hitoo Iwase
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  4. Suchen Li
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  5. Yu-Teh Li
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Van Halbeek, H., Vliegenthart, J.F.G., Iwase, H. et al. 1H-NMR spectroscopic characterization of dansyl glyco-asparagines derived from hen egg white clycoproteins. Glycoconjugate J 2, 235–253 (1985). https://doi.org/10.1007/BF01049271

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  • DOI: https://doi.org/10.1007/BF01049271

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