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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 7
BKCSDE 17(7)
July 20, 1996 

4-Deoxy-Analogs of p-Nitrophenyl β-D-Galactopyranosides for Specificity Study with β-Galactosidase from Escherichia coli
Shinsook Yoon, Hyoung Geun Kim, Keun Ho Chun, Jeong E. Nam Shin*
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.
599 - 604
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