𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of α- and β-l-Fuc p-(1 → 2)-α-l-Fuc p-(1 → 3)-β-d-Gal p NAc glycosides identified as termini of Schistosoma mansoni oligosaccharides

✍ Scribed by Vivekanand P. Kamath; Ole Hindsgaul

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
491 KB
Volume
280
Category
Article
ISSN
0008-6215

No coin nor oath required. For personal study only.

✦ Synopsis

Caulfield and colleagues have reported [1][2][3][4][5] that cercariae, the freshwater stage of Schistosoma mansoni that are infectious to humans, are covered by a 1-2 ~m-thick carbohydrate-rich glycocalyx layer that has immunomodulating properties. Structural studies carried out to identify the detailed carbohydrate structures have revealed that this glycocalyx is a complex structure composed of oligosaccharides with a high fucose content that are probably linked to a peptide. The proposed structures contain repeating units of a trifucosyl side chain attached to N-acetylglucosamine and terminated by an unusual linear difucosylated N-acetylgalactosamine sequence [6,7].

Mass-spectrometric structural studies utilizing fast atom bombardment ionization identified the terminal sequence as Fuc-(1 ~ 2)-Fuc-(1 ~ 3)-GalNAc [6,7]. Establishing the unambiguous anomeric configuration of these terminal glycosidic linkages will be greatly facilitated by having available reference standards to be used as substrates for fucosidases (in conjunction with mass spectral studies) or for ~H NMR chemical shift correlations. For these purposes, we have prepared two trisaccharides, namely a-L-

. We chose the aglycon, R = (CH2)aCOOMe, to permit the preparation of neoglycoproteins for eventual immunological studies.

📜 SIMILAR VOLUMES

2-bromoethyl glycosides in glycoside syn
2-bromoethyl glycosides in glycoside synthesis: Preparation of glycoproteins containing α-l-Fuc-(1→2)-d-Gal and β-d-Gal-(1→4)-d-GlcNAc
✍ Jan Dahmén; Torbjörn Frejd; Göran Magnusson; Ghazi Noori; Anne-Sofie Carlström 📂 Article 📅 1984 🏛 Elsevier Science 🌐 English ⚖ 808 KB

The applicability of 2-bromoethyl glycosides in carbohydrate synthesis is demonstrated by the synthesis of glycosides of a-L-Fuc-(1+2)-D-Gal and /?-D-Gal-(1+4)-D-GlcNAc. The bromoethyl aglycon was transformed into the methoxycarbonylethylthioethyl spacer, which allowed coupling of the sugars to prot

Synthesis of the glycosyl amino acids Nα
Synthesis of the glycosyl amino acids Nα-Fmoc-Ser[Ac4-β-d-Gal p-(1 → 3)-Ac2-α-d-GalN3 p]-OPfp and Nα-Fmoc-Thr[Ac4-β-d-Gal p-(1 → 3)-Ac2-α-d-GalN3 p]-OPfp and the application in the solid-phase peptide synthesis of multiply glycosylated mucin peptides with Tn and T antigenic structures
✍ Hans Paulsen; Stefan Peters; Tim Bielfeldt; Morten Meldal; Klaus Bock 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 952 KB

Two new glycosyl amino acids N'~-Fmoc-Ser[Ac4-fl-D-Galp-(1 ~ 3)-Ac2-a-D-GalN3P]-OPf p and N'~-Fmoc-Thr[Ac4-/3-D-Galp-(1 ~ 3)-Ac2-a-D-GalN3p]-OPf p were synthesized. Glycosylation of N'~-Fmoc-Ser-OPf p or N ~-Fmoc-Thr-OPfp with protected/3-o-Gal-( 1 -~ 3)-D-GaIN 3 donors afforded the glycosyl amino a

Oligosaccharides related to tumor-associ
Oligosaccharides related to tumor-associate antigens. Part 3. Synthesis of the propyl glycosides of the trisaccharide β-D-Galp-(1→3)-β-D-GalpNAc-(1→3)-α-D-Galp and of the Tetrasaccharide α-L-Fucp-(1→2)-β-D-Galp-(1→3)-β-D-GalpNAc-(1→3)-α-D-Galp, components of a tumor antigen recognized by the antibody MBr1
✍ Luigi Lay; Luigi Panza; Giovanni Russo; Diego Colombo; Fiamma Ronchetti; Elena A 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 German ⚖ 411 KB 👁 1 views

## Synthesis of the Propyl Glycosides of the TrisaccharideP-D-Galp-(l+3)-P-D-GalpNAc-(1+3)-a-D-Galp and of the Tetrasaccharide E-L-Fuc~-(~+~)-/?-D-Galp-(1+3)-j?-~-GalpNAc-(1+3)-a-D-Galp, Components of a Tumor Antigen ') part 2: [I].