Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tetlet.2003.10.178
Title: Convenient high yield and stereoselective synthesis of O-glycopeptides using N-α-Fmoc-Tyr/Ser[β-D-Glc(OAc)4]OPfp generated in solution
Authors: Gangadhar, B.P.
Jois, S.D.S. 
Balasubramaniam, A.
Keywords: NMR
O-Glycopeptides
Solid phase synthesis
Stereoselective
Issue Date: 5-Jan-2004
Source: Gangadhar, B.P., Jois, S.D.S., Balasubramaniam, A. (2004-01-05). Convenient high yield and stereoselective synthesis of O-glycopeptides using N-α-Fmoc-Tyr/Ser[β-D-Glc(OAc)4]OPfp generated in solution. Tetrahedron Letters 45 (2) : 355-358. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tetlet.2003.10.178
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.Et2O (6 equiv) in CH2Cl2 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. © 2003 Elsevier Ltd. All rights reserved.
Source Title: Tetrahedron Letters
URI: http://scholarbank.nus.edu.sg/handle/10635/105777
ISSN: 00404039
DOI: 10.1016/j.tetlet.2003.10.178
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