242474-08-4Relevant academic research and scientific papers
The synthesis of trisaccharides Neu5Ac(α2 → 6)[Gal(α1 → 3)]GalNAcα and Neu5Ac(α2 → 6)[Gal(β1 → 3)]GalNAcα as protected trifluoroacetamidopropyl glycosides
Simeoni,Byramova,Bovin
, p. 55 - 61 (2007/10/03)
Protected sialo-containing trisaccharides, fragments of oligosaccharide chains of mucin glycoproteins, were synthesized. Regioselective sialylation of the primary hydroxyl group of (3-fluoroacetamidopro-pyl)-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl)-α- D-galactopyranosyl)-α-D-galactopyranoside with methyl ester of peracetyl-β-ethylthioglycoside of N-acetylneuraminic acid in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid (or its trimethylsilyl ester) yielded 39 and 25% of α- and β-sialyl-(2 → 6)biosides, respectively. Catalytic hydrogenolysis of the azide and benzyl groups of the α-anomer followed by N- and O-acetylation gave target trifluoroacetamidopropyl glycoside, Neu5Ac(α2 → 6)[Gal(α1 → 3)]Gal-NAcα-OSp as a peracetate. An analogous coupling of the sialyl donor with (3-fluoroacetamidopropyl)-2-ace-tamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl)- β-D-galactopyranosyl)-α-D-galactopyranoside affords acetylated trifluoroacetamidopropyl glycoside Neu5Ac(α2 → 6)[Gal(β1 → 3)]GalNAcα-OSp in a yield of 15% and the corresponding Neu5Ac(β2 → 6)-anomer in a yield of 12%. After O-deacetylation and N-detrifluoro-acetylation, these sialylbiosides can be used as ligands in preparing neoglycoconjugates.
