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Automated solid-phase synthesis of oligosaccharides.

O J Plante1, E R Palmacci, P H Seeberger

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.

Science (New York, N.Y.)
|February 27, 2001
PubMed
Summary

Automated chemical synthesis now simplifies the creation of complex oligosaccharides. This method, similar to peptide synthesis, provides easier access to these crucial carbohydrate structures.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Biochemistry

Background:

  • Accessing structurally defined complex carbohydrates has historically been challenging and labor-intensive.
  • While solid-phase synthesis has advanced oligosaccharide construction, it still requires significant technical expertise.

Purpose of the Study:

  • To describe the automated chemical synthesis of complex oligosaccharides using solid-phase techniques.
  • To demonstrate a streamlined method for obtaining specific, complex carbohydrate structures.

Main Methods:

  • Utilized a solid-phase synthesizer for automated oligosaccharide construction.
  • Employed glycosyl phosphate building blocks and an octenediol-functionalized resin.
  • Synthesized a branched dodecasaccharide as a model complex carbohydrate.

Main Results:

  • Successfully automated the synthesis of several oligosaccharides.
  • Efficiently obtained the target branched dodecasaccharide after cleavage from the solid support.
  • Demonstrated the feasibility of automated synthesis for complex carbohydrate structures.

Conclusions:

  • Automated solid-phase synthesis significantly reduces the labor and expertise required for complex oligosaccharide production.
  • This approach makes complex carbohydrates accessible in a manner analogous to oligopeptides and oligonucleotides.
  • Paves the way for broader research and application of complex carbohydrates.

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