title: Isolation and identification of novel sulfated and nonsulfated oligosialyl glycosphingolipids from sea urchin sperm.
abstract: Novel sulfated and nonsulfated oligosialylglycosphingolipids were isolated from sperm of the sea urchin, Hemicentrotus pulcherrimus, and their structures were established as follows: [formula: see text] 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.
authors.affiliation: Department of Biophysics and Biochemistry, Graduate School of Science, University of Tokyo, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Ijuin
authors.forename: K
authors.initials: K
authors.lastname: Kitajima
authors.forename: Y
authors.initials: Y
authors.lastname: Song
authors.forename: S
authors.initials: S
authors.lastname: Kitazume
authors.forename: S
authors.initials: S
authors.lastname: Inoue
authors.forename: S M
authors.initials: SM
authors.lastname: Haslam
authors.forename: H R
authors.initials: HR
authors.lastname: Morris
authors.forename: A
authors.initials: A
authors.lastname: Dell
authors.forename: Y
authors.initials: Y
authors.lastname: Inoue
mesh_terms: D000818:Animals; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006028:Glycosphingolipids / Q000737:chemistry* / Q000302:isolation & purification; D008297:Male; D008745:Methylation; D008969:Molecular Sequence Data; D009439:Neuraminidase; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification; D012617:Sea Urchins; D012794:Sialic Acids / Q000032:analysis*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013094:Spermatozoa / Q000737:chemistry*
chemical_list: D006028:Glycosphingolipids; D009844:Oligosaccharides; D012794:Sialic Acids; D009439:Neuraminidase