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Chemical Compound Review:

AC1L3ELW 4-methyl-7-[(3R,4S,5S,6R)- 3,4,5-trihydroxy...

Synonyms: AR-1G3393, AC1Q69Y5, 18997-57-4, EINECS 242-736-7, 4-Methylumbelliferyl glucoside, ...

Morimoto, S. et al., Kuroki, G.W. et al., Shigematsu, H. et al., Boonclarm, D. et al., Rixon, J.E. et al., et al.

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Disease relevance of EINECS 242-736-7

A genomic library of Pseudomonas fluorescens subsp. cellulosa DNA constructed in pUC18 and expressed in Escherichia coli was screened for recombinants expressing 4-methylumbelliferyl beta-D-glucoside hydrolysing activity (MUGase) [1].
A patient with Gaucher's disease is described, in whom the disease could not be diagnosed enzymically in liver and leucocytes using artificial substrate 4-methylumbelliferyl beta-glucoside [2].

High impact information on EINECS 242-736-7

Similar to saposin C, saposin A stimulates the hydrolysis of 4-methylumbelliferyl beta-glucoside and glucocerebroside by beta-glucosylceramidase and of galactocerebroside by beta-galactosylceramidase, mainly by increasing the maximal velocity of both reactions [3].
The effect on the activity of galactosylceramide beta-galactosidase as well as 4-methylumbelliferyl-beta-glucoside beta-glucosidase in the twitcher brain and liver homogenates by authentic saposin A and C was similar to that in control tissues [4].
They also hydrolyzed at the same active site the synthetic substrates p-nitrophenyl-beta-D-glucoside and 4-methylumbelliferyl-beta-D-glucoside but were inactive towards (R)-prunasin, p-nitrophenyl-alpha-D-glucoside, and 4-methylumbelliferyl-alpha-D-glucoside [5].
This substrate was compared directly with 4-trifluoromethylumbelliferyl-beta-D-glucoside synthesized by us earlier and with 4-methylumbelliferyl-beta-D-glucoside which is commonly used for acid beta-glucosidase activity assay [6].
In fibroblasts from patients with Gaucher's disease, in vitro beta-glucosidase activities were 2.7-11.7% and 4.8-13.6% of control values when 4-methylumbelliferyl beta-D-glucoside and GlcSph were used as substrates, respectively [7].

Biological context of EINECS 242-736-7

Osteogenesis was inhibited when mandibular processes from 3 1/2-day-old embryos were cultured in BUdR, LACA, alpha, alpha'-Dipyridyl, 4-Methylumbelliferone, and 4-Methylumbelliferyl-beta-D-glucoside or beta-D-xyloside [8].

Anatomical context of EINECS 242-736-7

Compared with 4-methylumbelliferyl-beta-D-glucoside, HNGlu proves to be a highly specific substrate for glucocerebrosidase with little or no hydrolysis by the beta-glucosidases present in fibroblast extracts [9].
This report describes a reliable and reproducible method for the identification of carriers of Type I Gaucher disease using blood platelets as the source of beta-glucosidase and 4-methylumbelliferyl-beta-D-glucoside as substrate [10].

Associations of EINECS 242-736-7 with other chemical compounds

The negatively charged lipids, taurocholate and phosphatidylserine, were shown to be noncompetitive, nonessential activators of 4-methylumbelliferyl-beta-D-glucoside hydrolysis [11].
The enzymatic activity in both the particulate and solubilized fractions optimally hydrolyzed 4-methylumbelliferyl-beta-D-glucoside as well as the glycolipid substrate, glucosylceramide, at an acidic pH [12].
The enzyme showed poor hydrolysis of 4-methylumbelliferyl-beta-glucoside and esculin, and did not hydrolyze alkyl-beta-glucosides, glucobioses, cyanogenic-beta-glucosides, steroid beta-glucosides, nor other iridoid beta-glucosides [13].

References

Characterization of the gene celD and its encoded product 1,4-beta-D-glucan glucohydrolase D from Pseudomonas fluorescens subsp. cellulosa. Rixon, J.E., Ferreira, L.M., Durrant, A.J., Laurie, J.I., Hazlewood, G.P., Gilbert, H.J. Biochem. J. (1992) [Pubmed]
Pitfalls in the use of artificial substrates for the diagnosis of Gaucher's disease. Ben-Yoseph, Y., Nadler, H.L. J. Clin. Pathol. (1978) [Pubmed]
Saposin A: second cerebrosidase activator protein. Morimoto, S., Martin, B.M., Yamamoto, Y., Kretz, K.A., O'Brien, J.S., Kishimoto, Y. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
Saposins (sphingolipid activator proteins) in the twitcher mutant mouse. Shigematsu, H., Morimoto, S., Kishimoto, Y., Weiler, S., Tomich, J., Barranger, J., Shinohara, M., Yeager, A.M., O'Brien, J.S. J. Neurochem. (1990) [Pubmed]
Comparison of kinetic and molecular properties of two forms of amygdalin hydrolase from black cherry (Prunus serotina Ehrh.) seeds. Kuroki, G.W., Poulton, J.E. Arch. Biochem. Biophys. (1986) [Pubmed]
4-Pentafluoroethylumbelliferyl-beta-D-glucoside as a new fluorogenic substrate for acid beta-D-glucosidase. Tsvetkova, I.V., Karpova, E.A., Dudukina, T.V., Voznyi, Y.V. Clin. Chim. Acta (1996) [Pubmed]
Glucosylceramide and glucosylsphingosine metabolism in cultured fibroblasts deficient in acid beta-glucosidase activity. Sasagasako, N., Kobayashi, T., Yamaguchi, Y., Shinnoh, N., Goto, I. J. Biochem. (1994) [Pubmed]
The role of epithelial collagen and proteoglycan in the initiation of osteogenesis by avian neural crest cells. Bradamante, Z., Hall, B.K. Anat. Rec. (1980) [Pubmed]
An improved procedure for diagnosis of Gaucher disease using cultured skin fibroblasts and the chromogenic substrate, 2-hexadecanoylamino-4-nitrophenyl-beta-D-glucopyranoside. Barns, R.J., Clague, A.E. Clin. Chim. Acta (1982) [Pubmed]
Heterozygote detection of type I Gaucher disease using blood platelets. Nakagawa, S., Kumin, S., Sachs, G., Nitowsky, H.M. Clin. Chim. Acta (1982) [Pubmed]
Human lysosomal beta-glucosidase: kinetic characterization of the catalytic, aglycon, and hydrophobic binding sites. Grabowski, G.A., Gatt, S., Kruse, J., Desnick, R.J. Arch. Biochem. Biophys. (1984) [Pubmed]
Lysosomal beta-glucosidase of rat liver. Fabbro, D., Desnick, R.J., Gatt, S. Enzyme (1984) [Pubmed]
beta-Glucosidase catalyzing specific hydrolysis of an iridoid beta-glucoside from Plumeria obtusa. Boonclarm, D., Sornwatana, T., Arthan, D., Kongsaeree, P., Svasti, J. Acta Biochim. Biophys. Sin. (Shanghai) (2006) [Pubmed]

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