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Isolation and identification of novel sulfated and nonsulfated oligosialyl glycosphingolipids from sea urchin sperm

  • Papers Dedicated To Dr Sen-Itiroh Hakomori
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Abstract

Novel sulfated and nonsulfated oligosialyglycosphingolipids were isolated from sperm of the sea urchin,Hemicentrotus pulcherrimus, and their structures were established as follows: ±HSO3→Neu5Acα2→(8Neu5Acα2→)n→6G1cβ1→1´Cer, wheren=0, 1, 2, 3. This provides the first evidence for the natural occurrence of a tetrasialic acid structure in glycosphingolipids. The finding of sulfated oligosialyl chains is especially noteworthy in that the sulfate group exclusively resides on the C-8 of the nonreducing terminal residues of oligo/polysialyl chains and that sulfation appears to be a termination signal for elongation of oligosialyl chains. Sulfation at the nonreducing terminal Neu5Ac residues of oligosialyl chains was also found to facilitate the formation of an inter-residue lactone between the carboxyl group at the nonreducing terminal sulfated Neu5Ac and the hydroxyl group at C-9 of the penultimate Neu5Ac residue. The long chain base was 4-hydroxysphinganine (t18:0) and the major fatty acid species were identified as C20:1, C21:1, and C22:1.

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Abbreviations

C:M:

chloroform:methanol

FAB-MS:

fast atom bombardment mass spectrometry

GLC:

gas-liquid chromatography

GSL:

glycosphingolipid

HPTLC:

high performance thin-layer chromatography

Neu5Ac8HSO3 or HSO3 → Neu5Ac:

5-N-acetyl-8-O-sulforylneuraminic acid

Neu5Gc9HSO3 :

5-N-glycolyl-9-O-sulforylneuraminic acid

NMR:

nuclear magnetic resonance

PB:

sodium phosphate buffer, pH 7.2

Sia:

sialic acid

HSO3 → Sia:

sulfated sialic acid

polySia:

polysialic acid

TFA:

trifluoroacetic acid

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Author information

Author notes

  1. Yu Song

    Present address: The Biomembrane Institute, 201 Elliott Avenue West Suite 305, 98119-4230, Seattle, WA, USA

  2. Sadako Inoue & Yasuo Inoue

    Present address: Institute of Biological Chemistry, Academia Sinica, 115, Nangkang, Taipei, Republic of China

  3. Shinobu Kitazume

    Present address: Department of Biochemistry and Cell Biology, SUNY at Stony Brook, USA

Authors and Affiliations

  1. Department of Biophysics and Biochemistry, Graduate School of Science, University of Tokyo, Hongo-7, 113, Tokyo, Japan

    Takeshi Ijuin, Ken Kitajima, Yu Song, Shinobu Kitazume & Yasuo Inoue

  2. School of Pharmaceutical Sciences, Showa University, Hatanodai-1, 142, Tokyo, Japan

    Sadako Inoue

  3. Department of Biochemistry, Imperial College of Science, Technology and Medicine, SW7 2AZ, London, UK

    Stuart M. Haslam, Howard R. Morris & Anne Dell

Authors
  1. Takeshi Ijuin
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  2. Ken Kitajima
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  3. Yu Song
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  4. Shinobu Kitazume
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  5. Sadako Inoue
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  6. Stuart M. Haslam
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  7. Howard R. Morris
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  8. Anne Dell
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  9. Yasuo Inoue
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Additional information

Since the dividing line between oligo- and polysialic acids is not rigidly defined, we propose here that those containing more than penta-sialic acid chains can be referred to as the polysialic acid group. The rationale for this is that α2 → 8-linked pentasialic acid is the minimum chain length to exhibit the conformational property of polysialic acid [of Michon, F, Brisson, J-R, Jennings, H (1987)Biochemistry 26: 8399–405] and to act as a substrate for the endosialidase, Endo-N [Hallenbeck, PC, Vimr, ER, Yu, F, Bassler, B, Troy, FA (1987)J Biol Chem 262: 3553–61].

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Ijuin, T., Kitajima, K., Song, Y. et al. Isolation and identification of novel sulfated and nonsulfated oligosialyl glycosphingolipids from sea urchin sperm. Glycoconjugate J 13, 401–413 (1996). https://doi.org/10.1007/BF00731473

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  • DOI: https://doi.org/10.1007/BF00731473

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