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Unique disialosyl gangliosides from salmon kidney: Characterization of V3αFuc, IV3βGalNAc, II3(αNeuAc)2-Gg4Cer and its analogue with 4-O-acetyl-N-acetylneuraminic acid

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Abstract

Four unidentified acidic glycolipids (X3-X6) were isolated from the kidney of the Pacific salmon on an anion exchange column and by high performance liquid chromatography using a silica bead (Iatrobeads) column. Based on methylation analysis, chemical and enzymatic degradation, proton nuclear magnetic resonance spectroscopy and mass spectrometry, the glycon structure of X5 and X6 was identified as a unique disialosyl fucosyl-N-acetylgalactosaminyl ganglio-N-tetraose:

Fucα3GalNAcβ3Galβ3GalNAcβ4[NeuAcα8NeuAcα3] Galβ4Glcβ1Cer. NMR showed that X3 and X4 were analogues of X5 and X6 and contained O-acetyl groups on C4 of the outer N-acetylneuraminic acid, first disialosyl gangliosides containing 4-O-acetyl-N-acetylneuraminic acid. The ceramides of X3 and X5 contained predominantly C24: 1, and X4 and X6 contained saturated fatty acids (C14: 0, C16: 0 and C18: 0), whereas the long chain base was exclusively sphingenine. The concentrations of X3 and X4 were 0.13 and 0.16 nmol/g of kidney respectively and those of X5 and X6, were 0.07 nmol/g each.

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Abbreviations

GalNAc:

N-acetylgalactosamine

Fuc:

fucose

NeuAc:

N-acetylneuraminic acid

Cer:

ceramide

d18:1:

4-sphingenine

d18:0:

sphinganine

t18:0:

4-hydroxysphinganine

TLC:

thin layer chromatography

HPTLC:

high performance TLC

HPLC:

high performance liquid chromatography

GLC:

gas-liquid chromatography

GC-MS:

gas chromatography-mass spectrometry

1H-NMR:

proton nuclear magnetic resonance

1-D:

one-dimensional

2-D:

two-dimensional

COSY:

chemical shift correlated spectroscopy

LSIMS:

liquid secondary ion mass spectrometry

Me2SO:

dimethyl sulfoxide

BSTFA:

bis-(trimethylsilyl)trifluoroacetamide

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Authors and Affiliations

  1. Research Center of Biomedical Analysis and Radioisotope, Teikyo

    Yukio Niimura

  2. Department of Biochemistry, Teikyo University School of Medicine, 2-11-1, Kaga Itabashi-ku, Tokyo, 173-8605, Japan

    Ineo Ishizuka

Authors
  1. Yukio Niimura
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  2. Ineo Ishizuka
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Correspondence to Yukio Niimura.

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Niimura, Y., Ishizuka, I. Unique disialosyl gangliosides from salmon kidney: Characterization of V3αFuc, IV3βGalNAc, II3(αNeuAc)2-Gg4Cer and its analogue with 4-O-acetyl-N-acetylneuraminic acid. Glycoconj J 23, 489–499 (2006). https://doi.org/10.1007/s10719-006-6562-1

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  • DOI: https://doi.org/10.1007/s10719-006-6562-1

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