title: [Isomerization of trifluoroacetamidopropyl-2-acetamido-2-deoxy-D- galactopyranoside into alpha-anomer. A convenient method of synthesis of the artificial T-antigen].
abstract: Bioside Gal beta 1-3GalNAc alpha 1-O(CH2)3NHCOCF3 has been synthesized. The key alpha-glycoside GalNAc alpha 1-O(CH2)3NHCOCF3 (peracetate) was obtained either by isomerization of its beta-anomer with trifluoromethanesulfonic acid, or by direct glycosylation of 3-(trifluoroacetamido)propanol with D-galactosamine (anomeric pentaacetate) in the presence of a mixture of trifluoromethanesulfonic acid and boron trifluoride etherate. De-O-acetylated alpha-galactosaminide obtained was further transformed into benzylidene derivative, the latter was glycosylated with acetobromogalactose to give the protected alpha-bioside. The removal of the protecting groups gave the (3-aminopropyl)-alpha-bioside, which was subsequently immobilized on bovine serum albumin and cytochrome c.
mesh_terms: D000818:Animals; D015295:Antigens, Tumor-Associated, Carbohydrate; D055598:Chemical Phenomena; D002621:Chemistry; D004187:Disaccharides; D005688:Galactosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007114:Immunization; D007519:Isoantigens; D007536:Isomerism
chemical_list: D015295:Antigens, Tumor-Associated, Carbohydrate; D004187:Disaccharides; D007519:Isoantigens; C048999:trifluoroacetamidopropyl-2-acetamido-2-deoxygalactopyranoside; C016467:Thomsen-Friedenreich antigen; D005688:Galactosamine
vernacular_title: Izomerizatsiia triftoratsetamidopropil-2-atsetamido-2-dezoksi-beta- D-galaktopiranozida v alpha-anomer. Udobnyĭ metod sinteza iskusstvennogo T-antigena.