Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from <i>Ascaris suum</i>

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Abstract

<p>Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from <i>Ascaris suum</i> have been accomplished. Galα1→3GalNAcβ1→OR (<b>1</b>), Galβ1→3Galα1→3GalNAcβ1→OR (<b>2</b>), Galβ1→6Galα1→3GalNAcβ1→OR (<b>3</b>), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (<b>4</b>) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (<b>5</b>) (R = biotinylated probe) were synthesized by stepwise condensation (<b>1</b>–<b>4</b>) and block synthesis (<b>5</b>) using 5-(methoxycarbonylpentyl) 2-<i>O</i>-benzoyl-3-<i>O</i>-2-napthylmethyl-4,6-<i>O</i>-di-<i>tert</i>-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-<i>O</i>-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (<b>12</b>) as a common precursor. Compound <b>12</b> was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively.</p>

Journal

  • Chemical and Pharmaceutical Bulletin

    Chemical and Pharmaceutical Bulletin 67(2), 143-154, 2019

    The Pharmaceutical Society of Japan

Codes

  • NII Article ID (NAID)
    130007600919
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • ISSN
    0009-2363
  • NDL Article ID
    029481626
  • NDL Call No.
    Z53-D167
  • Data Source
    NDL  J-STAGE 
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