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Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides gd3, gt3, gm2, gd2, gt2, gm1, and gd1a

Academic Article
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Overview

authors

  • Blixt, O.
  • Vasiliu, D.
  • Allin, K.
  • Jacobsen, N.
  • Warnock, D.
  • Razi, N.
  • Paulson, James
  • Bernatchez, S.
  • Gilbert, M.
  • Wakarchuk, W.

publication date

  • September 2005

journal

  • Carbohydrate Research  Journal

abstract

  • We have synthesized several ganglio-oligosaccharide structures using glycosyltransferases from Campylobacter jejuni. The enzymes, alpha-(2-->3/8)-sialyltransferase (Cst-II), beta-(1-->4)-N-acetylgalactosaminyltransferase (CgtA), and beta-(1-->3)-galactosyltransferase (CgtB), were produced in large-scale fermentation from Escherichia coli and further characterized based on their acceptor specificities. 2-Azidoethyl-glycosides corresponding to the oligosaccharides of GD3 (alpha-D-Neup5Ac-(2-->8)-alpha-D-Neup5Ac-(2-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-), GT3 (alpha-D-Neup5Ac-(2-->8)-alpha-D-Neup5Ac-(2-->8)-alpha-D-Neup5Ac-(2-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-), GM2 (beta-D-GalpNAc-(1-->4)-[alpha-D-Neup5Ac-(2-->3)]-beta-D-Galp-(1-->4)-beta-D-Glcp-), GD2 (beta-D-GalpNAc-(1-->4)-[alpha-D-Neup5Ac-(2-->8)-alpha-D-Neup5Ac-(2-->3)]-beta-D-Galp-(1-->4)-beta-D-Glcp-), GT2 (beta-D-GalpNAc-(1-->4)-[alpha-D-Neup5Ac-(2-->8)-alpha-D-Neup5Ac-(2-->8)-alpha-D-Neup5Ac-(2-->3)]-beta-D-Galp-(1-->4)-beta-D-Glcp-), and GM1 (beta-D-Galp-(1-->3)-beta-D-GalpNAc-(1-->4)-[alpha-D-Neup5Ac-(2-->3)]-beta-D-Galp-(1-->4)-beta-D-Glcp-) were synthesized in high yields (gram-scale). In addition, a mammalian alpha-(2-->3)-sialyltransferase (ST3Gal I) was used to sialylate GM1 and generate GD1a (alpha-D-Neup5Ac-(2-->3)-beta-D-Galp-(1-->3)-beta-D-GalpNAc-(1-->4)-[alpha-D-Neup5Ac-(2-->3)]-beta-D-Galp-(1-->4)-beta-D-Glcp-) oligosaccharide. We also cloned and expressed a rat UDP-N-acetylglucosamine-4'epimerase (GalNAcE) in E. coli AD202 cells for cost saving in situ conversion of less expensive UDP-GlcNAc to UDP-GalNAc.

subject areas

  • Escherichia coli
  • G(M2) Ganglioside
  • Galactosyltransferases
  • Gangliosides
  • Lactosylceramides
  • N-Acetylgalactosaminyltransferases
  • Sialyltransferases
  • Substrate Specificity
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Research

keywords

  • chemoenzymatic
  • ganglioside
  • glycosyltransferase
  • oligosaccharide
  • synthesis
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Identity

International Standard Serial Number (ISSN)

  • 0008-6215

Digital Object Identifier (DOI)

  • 10.1016/j.carres.2005.06.008

PubMed ID

  • 16005859
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Additional Document Info

start page

  • 1963

end page

  • 1972

volume

  • 340

issue

  • 12

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