Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tetlet.2003.10.178
DC FieldValue
dc.titleConvenient 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.authorGangadhar, B.P.
dc.contributor.authorJois, S.D.S.
dc.contributor.authorBalasubramaniam, A.
dc.date.accessioned2014-10-29T01:50:36Z
dc.date.available2014-10-29T01:50:36Z
dc.date.issued2004-01-05
dc.identifier.citationGangadhar, 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.issn00404039
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/105777
dc.description.abstractFmoc-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.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.tetlet.2003.10.178
dc.sourceScopus
dc.subjectNMR
dc.subjectO-Glycopeptides
dc.subjectSolid phase synthesis
dc.subjectStereoselective
dc.typeArticle
dc.contributor.departmentPHARMACY
dc.description.doi10.1016/j.tetlet.2003.10.178
dc.description.sourcetitleTetrahedron Letters
dc.description.volume45
dc.description.issue2
dc.description.page355-358
dc.description.codenTELEA
dc.identifier.isiut000187867200029
Appears in Collections:Staff Publications

Show simple item record
Files in This Item:
There are no files associated with this item.

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.