96093-11-7Relevant academic research and scientific papers
Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
Keith, D. Jamin,Townsend, Steven D.
supporting information, p. 12939 - 12945 (2019/08/22)
Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
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.
Regioselective glycosylation of glucosamine and galactosamine derivates using O-pivaloyl galactosyl donors
O?wald, Mathias,Lang, Uwe,Friedrich-Bochnitschek, Siglinde,Pfrengle, Waldemar,Kunz, Horst
, p. 764 - 774 (2007/10/03)
Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield. With 4,6-O-benzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.
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 (2007/10/02)
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
