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2-Deoxi-2-trifluoroacetamido-β-D-glucopyranosyl fluoride in the synthesis of fluorogenic α- and β-N-acetylglucosaminides
Y. V. Voznyi, S. V. Afanasyeva, I. S. Kalicheva, A. A. Galoyan
Institute of Biochemistry, Academy of Sciences of the Armenian Republic, Erevan
Abstract: Using 2-deoxy-2-amino-D-glucopyranose hydrochloride as starting material, ethyl trifluoroacetate and 2,4,6-collidine hydrofluoride as key reagents, the synthesis of 2-deo-xy-2-trifluoroacetamido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl fluoride was performed. Reactions of this fluoride with TMS-ethers of 4-methyl- and 4-trifluoromethyl-7-hydro-xycoumarine lead to anomeric mixtures of aryl glucosaminide easily separated by column chromatography. After removal of O-acetyl groups and transformation of N-trifluoroacetyl- into N-acetyl groups, fluorogenic substrates suitable for determination of α-N-acetyl- and β-N-acetylglucosaminidases was obtained. The structures of the previously unknown derivatives were confirmed by 1H and 13C NMR spectroscopy.
Russian Journal of Bioorganic Chemistry 1991, 17 (9):1251-1257