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Sugar-assisted ligation in glycoprotein synthesis.

Yu-Ying Yang1, Simon Ficht, Ashraf Brik

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Journal of the American Chemical Society
|May 26, 2007
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Summary

Sugar-assisted ligation (SAL) now synthesizes alpha-O-linked glycoproteins and glycopeptides. This method enables the creation of complex glycoproteins, including those with cysteine residues, expanding its utility in chemical synthesis.

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Area of Science:

  • Chemical Synthesis
  • Glycochemistry
  • Biochemistry

Background:

  • Sugar-assisted ligation (SAL) is effective for synthesizing beta-O-linked and N-linked glycopeptides.
  • Extending SAL's utility to alpha-O-linked glycopeptides and glycoproteins is a significant advancement.

Purpose of the Study:

  • To develop a novel chemical synthetic route for the alpha-O-linked glycoprotein diptericin epsilon using SAL.
  • To demonstrate the general applicability of SAL in glycoprotein synthesis, including cysteine-containing glycopeptides.

Main Methods:

  • Utilized SAL for initial ligation of diptericin segments.
  • Employed native chemical ligation (NCL) for full sequence assembly after deprotection.
  • Applied hydrogenolysis for thiol removal and conversion of mutated cysteine to alanine.

Main Results:

  • Successfully synthesized the alpha-O-linked glycoprotein diptericin epsilon.
  • Demonstrated selective desulfurization of sugar moieties in the presence of Acm-protected cysteine.
  • Established SAL as a versatile tool for synthesizing diverse glycoproteins.

Conclusions:

  • SAL is a powerful and generalizable method for the chemical synthesis of alpha-O-linked glycoproteins.
  • This approach broadens the scope of SAL for creating complex glycopeptides and glycoproteins, including those with cysteine residues.