124167-44-8Relevant academic research and scientific papers
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).
