[Isomerization of trifluoroacetamidopropyl-2-acetamido-2-deoxy-D- galactopyranoside into alpha-anomer. A convenient method of synthesis of the artificial T-antigen].

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.