94452-17-2

Usage

Uses

A specific fluorogenic substrate of galactocerebrosidase for the diagnosis of Krabbe disease.

InChI:InChI=1/C32H49NO9/c1-4-5-6-7-8-9-10-11-12-13-14-15-20(2)31(39)33-23-17-22-21(3)16-27(35)40-24(22)18-25(23)41-32-30(38)29(37)28(36)26(19-34)42-32/h16-18,20,26,28-30,32,34,36-38H,4-15,19H2,1-3H3,(H,33,39)/t20?,26-,28+,29+,30-,32-/m1/s1

Upstream product

• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 112-67-4 n-hexadecanoyl chloride 
• 113808-19-8 Sodium; 6-hexadecanoylamino-4-methyl-2-oxo-2H-chromen-7-olate 
• 99422-73-8 6-Hexadecanoylamino-4-methylumbelliferone 
• 68047-36-9 6-amino-7-hydroxy-4-methyl-2H-chromen-2-one 
• 99542-01-5 6-Hexadecanoylamino-4-methylumbelliferyl-β-O-tetraacetylgalactopyranoside 

Relevant academic research and scientific papers

The use of glycosides of 6- and 8-acylamino-4-methylumbelliferone in studies of the specificity and properties of human lyosomal glycolipid hydrolases

A series of 6- and 8-acylamino-4-methylumbelliferyl β-D-galactopyranosides, β-D-glucopyranosides, and α-L-fucopyranosides having various fatty acyl residues were synthesized; 6- (9) and 8-hexadecanoylamino-4-methylumbelliferyl β-D-galactopyranoside (10) were shown to be substrates for human galactocerebrosidase.Analogs of 9 with shorter acid residues (octanoyl and butanoyl) were substrates for another type of β-D-galactosidase, i.e., GM1-ganglioside-β-D-galactosidase.The specificity of various β-D-galactosidases for synthetic D-galactopyranosides, differing in the length and position of their acylamide residue, tested with enzyme preparations from patients with two types of glycolipidosis, Krabbe's disease (galactocerebrosidase and GM1-β-galactosidase deficiency), suggested that 9 is a specific substrate for galactocerebrosidase in biochemical tests for Krabbe's disease.Fluorogenic 6-octanoyl- and 6-hexadecanoyl-amino-4-methylumbelliferyl β-D-glucopyranoside were much less readily hydrolyzed by both human and animal glucocerebrosidase than chromogenic 2-hexadecanoylamino-4-nitrophenyl β-D-glucopyranoside.Comparison of the hydrolysis of 4-methylumbelliferyl α-L-fucopyranoside with that of 6-hexadecanoylamino-4-methylumbelliferyl α-L-fucopyranoside by multiple forms of human α-L-fucosidase showed that the enzyme is capable of hydrolyzing not only hydrophilic but also synthetic, lipid-like substrates.

GLYCOSYLATION OF o-ACYLAMINO DERIVATIVES OF 4-METHYL-7-HYDROXY-COUMARIN

Certain glycopyranosides of o-acylamino-4-methyl-7-hydroxycoumarin were studied.They have potential application as fluorogenic substrates for a number of enzymes in biochemical diagnostics of hereditary diseases.