2-Trifluoro-acetamido-2-deoxy-β-D-galactopyranosyl fluoride as a new glucosylating agent in the synthesis of chromogenic and fluorogenic substrates of α- and β-N-acetylgalactosaminidases
Ya. V. Voznyi, S. V. Afanasyeva, I. S. Kalicheva, A. A. Galoyan
Institute of Biochemistry, Academy of Sciences of the Armenian Republic, Erevan
Abstract: 2-Trifluoroacetamido-2-deoxy-β-D-galactopyranosyl fluoride has been prepared in 50% yield by the four-step synthesis with the usb of ethyl trifluoroacetate as N-tri-fluoroacetylating reagent. Reactions of this fluoride with trimethylsilyl ethers of p-nitro-phenole, 4-methyl-, and 4-trifluoromethylumbelliferone followed by removal of O-sub-stituents and modification of N-protecting groups are proposed for synthesis of N-acetyl-galactosaminidase substrates. Anomeric pairs of N-trifluoroacetyl glycosides produced with the overall yield 51–67% have been easily separated by column chromatography, α-anomers being isolated with 17–20% yields. The structures of the previously undescribed substances are confirmed by 13C NMR spectroscopy.
Russian Journal of Bioorganic Chemistry 1991, 17 (4):510-516