Please use this identifier to cite or link to this item:
https://doi.org/10.1016/j.tetlet.2003.10.178
DC Field | Value | |
---|---|---|
dc.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 | |
dc.contributor.author | Gangadhar, B.P. | |
dc.contributor.author | Jois, S.D.S. | |
dc.contributor.author | Balasubramaniam, A. | |
dc.date.accessioned | 2014-10-29T01:50:36Z | |
dc.date.available | 2014-10-29T01:50:36Z | |
dc.date.issued | 2004-01-05 | |
dc.identifier.citation | 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 | |
dc.identifier.issn | 00404039 | |
dc.identifier.uri | http://scholarbank.nus.edu.sg/handle/10635/105777 | |
dc.description.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. | |
dc.description.uri | http://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.tetlet.2003.10.178 | |
dc.source | Scopus | |
dc.subject | NMR | |
dc.subject | O-Glycopeptides | |
dc.subject | Solid phase synthesis | |
dc.subject | Stereoselective | |
dc.type | Article | |
dc.contributor.department | PHARMACY | |
dc.description.doi | 10.1016/j.tetlet.2003.10.178 | |
dc.description.sourcetitle | Tetrahedron Letters | |
dc.description.volume | 45 | |
dc.description.issue | 2 | |
dc.description.page | 355-358 | |
dc.description.coden | TELEA | |
dc.identifier.isiut | 000187867200029 | |
Appears in Collections: | Staff Publications |
Show simple item record
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.