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4-Deoxy-Analogs of p-Nitrophenyl $\beta$-D-Galactopyranosides for Specificity Study with $\beta$-Galactosidase from Escherichia coli

  • Published : 1996.07.20

Abstract

The synthesis is reported of p-nitrophenyl glycosides of D-galactose modified at C-4 with azido- (5), amino- (6) group and fluorine (13). 4-Azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-galactopyranosyl chloride and 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-α-D-galactopyranosyl bromide were coupled with potassium p-nitrophenoxide in the presence of 18-crown-6 giving the corresponding p-nitrophenyl 4-azido-and 4-fluoro-4-deoxy-β-D-galactopyranoside derivatives. p-Nitrophenyl 4-amino-4-deoxy-β-D-galactopyranoside (6) was obtained by selective reduction of p-nitrophenyl 4-azido-4-deoxy-β-D-galactopyranoside (5) using 1,3-propane dithioltriethylamine. These galactoside analogs were slowly hydrolyzed in the increasing rate order of 5, 6 and 13 by β-galactosidase from Escherichia coli.

Keywords

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