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Convenient high yield and stereoselective synthesis ofO-glycopeptides usingN-α-Fmoc-Tyr/Ser[β-d-Glc(OAc)4]OPfp generated in solution

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
2
Identifiers
DOI: 10.1016/j.tetlet.2003.10.178
Keywords
  • O-Glycopeptides
  • Solid Phase Synthesis
  • Stereoselective
  • Nmr

Abstract

Abstract Fmoc-AA-OPfp (AA=Tyr or Ser) (1 equiv) was reacted with β- d-Glc(OAc) 5 (6 equiv) in the presence of BF 3.Et 2O (6 equiv) in CH 2Cl 2 at room temperature for 2 h, and the glycosylation reaction mixture was used directly to couple to the amino group of the peptide resin without isolation and purification of the Fmoc-AA[β- d-Glc(OAc) 4]-OPfp. Moreover, the -OAc protecting groups of glucose was removed just prior to releasing the peptide from the resin using 6 mM NaOMe in 85% DMF-MeOH. The crude product obtained by TFA cleavage contained >90% of the target O-glycopeptide, and the 500 MHz 1H NMR analysis revealed that the glycosylation reaction was nearly stereoselective (>97% β-anomer). This method is rapid and stereoselective, and can now be exploited for the routine synthesis of O-glycopeptides.

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