Glycoconjugate Journal

, Volume 13, Issue 3, pp 401–413

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

  • Takeshi Ijuin
  • Ken Kitajima
  • Yu Song
  • Shinobu Kitazume
  • Sadako Inoue
  • Stuart M. Haslam
  • Howard R. Morris
  • Anne Dell
  • Yasuo Inoue
Papers Dedicated To Dr Sen-Itiroh Hakomori

DOI: 10.1007/BF00731473

Cite this article as:
Ijuin, T., Kitajima, K., Song, Y. et al. Glycoconjugate J (1996) 13: 401. doi:10.1007/BF00731473

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.

Keywords

oligosialoglycosphingolipidsulfated sialic acidsea urchin sperm

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

Copyright information

© Chapman & Hall 1996

Authors and Affiliations

  • Takeshi Ijuin
    • 1
  • Ken Kitajima
    • 1
  • Yu Song
    • 1
  • Shinobu Kitazume
    • 1
  • Sadako Inoue
    • 2
  • Stuart M. Haslam
    • 3
  • Howard R. Morris
    • 3
  • Anne Dell
    • 3
  • Yasuo Inoue
    • 1
  1. 1.Department of Biophysics and Biochemistry, Graduate School of ScienceUniversity of TokyoTokyoJapan
  2. 2.School of Pharmaceutical SciencesShowa UniversityTokyoJapan
  3. 3.Department of BiochemistryImperial College of Science, Technology and MedicineLondonUK
  4. 4.The Biomembrane InstituteSeattleUSA
  5. 5.Institute of Biological ChemistryAcademia SinicaNangkang, TaipeiRepublic of China
  6. 6.Department of Biochemistry and Cell BiologySUNY at Stony BrookUSA