C. S. Jones, R. H. Shah, D. Kosman
Sep 1, 1974
Citations
0
Influential Citations
17
Citations
Journal
Carbohydrate research
Abstract
Abstract p -Aminophenyl 2-acetamido-2-deoxy-1-thio-β- D -glucopyranoside and -galactopyranoside were synthesized for use as ligands in the purification of 2-acetamido-2-deoxy-β- D -glucosidase, from Aspergillus niger and Phaseolus vulgaris , by affinity chromatography. The condensation of 2-acetamido-1,3,4,6-tetra- O -acetyl-2-deoxy-α- D -glucose and -β- D -galactose with p -nitrothiophenol in the presence of zinc chloride afforded p -nitrophenyl 2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-1-thio-β- D -glucopyranoside and -galactopyranoside, respectively. The former was also obtained by the reaction of 2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-α- D -glucopyranosyl chloride with p -nitrothiophenol in the presence of potassium hydroxide. O -Deacetylation followed by reduction with hydrogen over palladium on barium sulfate gave the p -aminophenyl 2-acetamido-2-deoxy-1-thio-β- D -glucopyranoside and -galactopyranoside. Inhibition constants ( K i ) of the p -nitrophenyl and p -aminophenyl 2-acetamido-2-deoxy-1-thio-β- D -glucosides and -galactosides for A. niger 2-acetamido-2-deoxy-β- D -glucosidase were determined by using p -nitrophenyl 2-acetamido-2-deoxy-β- D glucopyranoside and -galactopyranoside as substrates.