Glycoconjugate Journal

, Volume 32, Issue 9, pp 729–734 | Cite as

Preparation of legionaminic acid analogs of sialo-glycoconjugates by means of mammalian sialyltransferases

  • David C. Watson
  • Warren W. Wakarchuk
  • Christian Gervais
  • Yves Durocher
  • Anna Robotham
  • Steve M. Fernandes
  • Ronald L. Schnaar
  • N. Martin Young
  • Michel Gilbert
Original Article

Abstract

Legionaminic acids are analogs of sialic acid that occur in several bacteria. The most commonly occurring form is Leg5Ac7Ac, which differs from Neu5Ac only at the C7 (acetamido) and C9 (deoxy) positions. While these differences greatly reduce the susceptibility of Leg compounds to sialidases, several sialyltransferases have been identified that can use CMP-Leg5Ac7Ac as a donor (Watson et al. 2011). We report the successful modification with Leg5Ac7Ac of a glycolipid, GM1a, and two glycoproteins, interferon-α2b and α1-antitrypsin, by means of two mammalian sialyltransferases, namely porcine ST3Gal1 and human ST6Gal1. The Leg5Ac7Ac form of GD1a was not recognized by the myelin-associated glycoprotein (MAG, Siglec-4), confirming the importance of the glycerol moiety in the interaction of sialo-glycans with Siglecs.

Keywords

α1-antitrypsin GD1a Human ST6Gal1 sialyltransferase Interferon-α2b Porcine ST3Gal1 sialyltransferase 

Abbreviations

FCHASE

6-(fluorescein-5-carboxyamido)-hexanoic acid succinimidyl ester derivative of the p-aminophenyl glycoside

LacNAc

Galβ1-4GlcNAc.

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Copyright information

© Her Majesty the Queen in Right of Canada as represented by: NRC Canada 2015

Authors and Affiliations

  • David C. Watson
    • 1
  • Warren W. Wakarchuk
    • 2
  • Christian Gervais
    • 3
  • Yves Durocher
    • 3
  • Anna Robotham
    • 1
  • Steve M. Fernandes
    • 4
  • Ronald L. Schnaar
    • 4
  • N. Martin Young
    • 1
  • Michel Gilbert
    • 1
  1. 1.Human Health TherapeuticsNational Research Council CanadaOttawaCanada
  2. 2.Department of Chemistry and BiologyRyerson UniversityTorontoCanada
  3. 3.Human Health TherapeuticsNational Research Council CanadaMontrealCanada
  4. 4.Department of PharmacologyJohns Hopkins School of MedicineBaltimoreUSA

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