36476-29-6Relevant academic research and scientific papers
Profiling of glycosidase activities using coumarin-conjugated glycoside cocktails
Park, Sungjin,Shin, Injae
, p. 619 - 622 (2007/10/03)
Glycosidases are a large subgroup of carbohydrate-processing enzymes that hydrolytically cleave the glycosidic bond. Glycans formed by the action of glycosidases are involved in various biological processes. Genetic abnormalities in glycosidases are associated with inherited diseases. Thus, characterization of the catalytic activities of glycosidases is of great importance. Herein, we describe a simple and rapid approach for determining glycosidase activity profiles using coumarin-conjugated glycoside cocktails.
Synthesis of 4-methylumbelliferyl glycosides for the detection of α- and β-D-galactopyranosaminidases
Szweda, R.,Spohr, U.,Lemieux, R. U.,Schindler, D.,Bishop, D. F.,Desnick, R. J.
, p. 1388 - 1391 (2007/10/02)
Reaction at room temperature of either 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α- of β-D-galactopyranosyl chloride with a twofold excess of 4-methylumbelliferone and silver trifluoromethanesulfonate in dichloromethane containing an equimolar amount of sym-collidine yielded 4-methylumbelliferyl tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside in 33percent yield.The β anomer was formed in 20 and 10percent yields, respectively.Reduction of the azido group, acetylation followed by de-O-acetylation, provided the desired 4-methylumbelliferyl 2-acetamido-2-deoxy-α- and β-D-galactopyranosides (N-acetyl-α- and β-D-galactopyranosaminides).The α-glycoside proved to be an effective substrate for the highly sensitive fluorimetric detection of N-acetyl-α-D-galactopyranosaminidase activity in human tissues and was used to examine the deficiency of this activity, which is the enzymatic defect in Schindler disease.Key words: synthesis of 4-methylumbelliferyl N-acetyl-α- and β-D-galactopyranosaminides, N-acetyl-α-D-galactosaminidase deficiency (Schindler disease).
