191341-73-8Relevant academic research and scientific papers
Synthesis of the glycosyl amino acids Nα-Fmoc-Ser3)-Ac2-α-D-GalN3p>-OPfp and Nα-Fmoc-Thr3)-Ac2-α-D-GalN3p>-OPfp and the application in the solid-phase peptide synthesis of multiply glycosylated mucin peptides with Tn and T antigenic stru...
Paulsen, Hans,Peters, Stefan,Bielfeldt, Tim,Meldal, Morten,Bock, Klaus
, p. 17 - 34 (1995)
Two new glycosyl amino acids Nα-Fmoc-Ser3)-Ac2-α-D-GalN3p>-OPfp and Nα-Fmoc-Thr3)-Ac2-α-D-GalN3p>-OPfp were synthesized.Glycosylation of Nα-Fmoc-Ser-OPfp or Nα-Fmoc-Thr-OPfp with protected β-D-Gal-(13)-D-GalN3 donors afforded the glycosyl amino acids containing an activated C-terminus which could be utilized directly for solid-phase glycopeptide synthesis.The transformation of the 2-azido group into the acetamido derivative was achieved quantitatively at the end of the synthesis by treatment of the polymer-bound glycopeptide with thioacetic acid.The versatility of this strategy was demonstrated by the assembly of eight triply glycosylated mucin peptides which were synthesized simultaneously by multiple column techniques.The glycopeptides were prepared in order to investigate the substrate specificity of a galactosyltransferase. Keywords: Glycopeptides; Synthesis; Carbohydrates; Solid-phase glycopeptide synthesis
Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen
Renaudet, Olivier,Dumy, Pascal
, p. 65 - 68 (2007/10/03)
The first synthesis of the tumor-associated α-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective.
Synthesis of TN and T Antigen Glycopeptide Sequences of Tumor-Associated MUC-1 Using S-Pent-4-enyl Thioglycosides
Leuck, Michael,Kunz, Horst
, p. 322 - 334 (2007/10/03)
The syntheses of glycopeptides34 and 38 with tumor associated TN and T antigen structure containing a partial sequence of the tandem repeat unit of the polymorphic epithelial mucin MUC-1 were achieved via fragment condensations. Electrophilic a
