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Solid-phase synthesis of complex oligosaccharides using a novel capping reagent.

Xiangyang Wu1, Richard R Schmidt

  • 1Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.

The Journal of Organic Chemistry
|April 3, 2004
PubMed
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This study reports efficient solid-phase synthesis of complex N-glycans, including the Galili antigen trisaccharide. The novel approach simplifies purification, yielding target molecules with minimal byproducts.

Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Glycobiology

Background:

  • Oligosaccharide synthesis is crucial for understanding biological processes.
  • Developing efficient solid-phase methods remains a key challenge in glycochemistry.
  • Complex N-glycans and specific antigens like Galili are important targets.

Purpose of the Study:

  • To develop a robust solid-phase strategy for synthesizing core N-glycan tetrasaccharides.
  • To synthesize a trisaccharide containing the Galili antigen using solid-phase techniques.
  • To establish a convenient and efficient purification process for synthesized oligosaccharides.

Main Methods:

  • Utilized a hydroxymethylbenzyl benzoate spacer-linker system on Merrifield resin.
  • Employed O-Fmoc-protected O-glycosyl trichloroacetimidates as glycosyl donors.

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  • Applied benzoyl isocyanate as a capping reagent for unreactive hydroxyl groups.

    • Main Results:

    • Successfully synthesized a core N-glycan tetrasaccharide.
    • Efficiently produced a trisaccharide containing the Galili antigen.
    • Achieved high yields with minimal byproduct formation, simplifying purification.

    Conclusions:

    • The developed solid-phase methodology enables efficient synthesis of complex oligosaccharides.
    • The strategy is suitable for producing biologically relevant glycans, including the Galili antigen.
    • Convenient purification facilitates the accessibility of these important carbohydrate structures.