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Structure determination of a sulfated N-glycans, candidate for a precursor of the selectin ligand in bovine lung

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Abstract

To clarify the structure of non-sialic acid anionic residue on N-glycans in the mammalian tissues, we have isolated sialidase-resistant anionic residue on N-glycans from bovine lung. Analyses by partial acid hydrolysis and glycosidase digestions combined with a two-dimensional HPLC mapping method revealed that the major sialidase-resistant anionic N-glycan had a fucosylbianntenary core structure. The anionic residue was identified as a sulfate ester by methanolysis, anion-exchange chromatography, and mass spectrometry. The linkage position of the sulfate ester was the 6-position of the GlcNAc residue on the Manα1-6 branch. This conclusion was based on the results of glycosidase digestions followed by two-dimensional HPLC mapping. Furthermore, the disialylated form of this sulfated glycan was dominant, and no asialo form was detected. The structure of the major anionic N-glycan prepared from bovine lung and having a sulfate was proposed to be the pyridylamino derivative of Siaα2-3Gαlβ1-4(HSO3-6)GlcNAcβ1-2Manα1-6(Siaα2-3Galβ1-4GlcNAcβ1-2Manα1-3)Manβ1-4GlcNAcβ1-4(Fucα1-6)GlcNAc.

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Abbreviations

HPLC:

high performance liquid chromatography

MALDI:

matrix assisted laser desorption ionization

MS:

mass spectrometry

PA:

pyridylamino

TOF:

time of flight

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Acknowledgements

This work was supported in part by a grant-in-aid from the Japan Health Science Foundation and from the 21st Century COE (Creation of Integrated EcoChemistry) and Protein 3000 programs of the Ministry of Education, Science, Sports, and Culture of Japan for S. H., and CREST of the Japan Science and Technology Agency for S. N.

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Authors and Affiliations

  1. Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan

    Tomonori Murakami, Shunji Natsuka, Shin-ichi Nakakita & Sumihiro Hase

  2. Department of Functional Glycomics, Life Science Research Center, Kagawa University, Kita-gun, Kagawa, 761-0793, Japan

    Shin-ichi Nakakita

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  1. Tomonori Murakami
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  2. Shunji Natsuka
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  4. Sumihiro Hase
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Correspondence to Sumihiro Hase.

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Murakami, T., Natsuka, S., Nakakita, Si. et al. Structure determination of a sulfated N-glycans, candidate for a precursor of the selectin ligand in bovine lung. Glycoconj J 24, 195–206 (2007). https://doi.org/10.1007/s10719-006-9026-8

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