| Autor: |
Szweda, R., Spohr, U., Lemieux, R. U., Schindler, D., Bishop, D. F., Desnick, R. J. |
| Zdroj: |
Canadian Journal of Chemistry; September 1989, Vol. 67 Issue: 9 p1388-1391, 4p |
| Abstrakt: |
Reaction at room temperature of either 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α- or -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 33% yield. The β anomer was formed in 20 and 10% 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. Keywords: synthesis of 4-methylumbelliferyl N-acetyl-α- and -β-D-galactopyranosaminides, N-acetyl-α-D-galactosaminidase deficiency (Schindler disease). |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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