Conduritol B Epoxide

CATALOG # 1889
Amount 25 mg
Price $270.00
Qty
 
Conduritol B Epoxide
  • Catalog #:1889
  • Scientific Name:Conduritol B Epoxide
  • Common Name:D,L-1,2-Anhydro-myo-inositol;
    Activity: Inhibits alpha-glucosidase activity; specific inhibitor of glucocerebrosidase in cultured cells
  • Empirical Formula:C6H10O5
  • CAS#6090-95-5
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:162
  • Unit:25 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, identity confirmed by MS
  • Natural Source:n/a
  • Melting Point:164-166°C
  • Solubility:water, DMSO, methanol (slightly)
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    Conduritol B epoxide (CBE) is a derivative of the naturally occurring conduritol B and is a catalytic, site-directed, covalent inhibitor of acid beta-glucosidase1 and of alpha-glucosidase.2 Conduritol B epoxide binds covalently and irreversibly to the catalytic site of acid beta-glucosidase, which is the enzyme responsible for the conversion of glucosylceramide to ceramide.3 Gaucher disease, the most prevalent lysosomal storage disease, is caused by mutations in the gene encoding acid betaglucosidase resulting in a defect in the enzyme beta-glucosidase activity and a subsequent accumulation of glucosylceramide. Conduritol B epoxide can be used to rapidly reproduce the effects of Gaucher disease making it ideal for studies of this condition.4 Treatment with CBE results in glucocerebrosides accumulating in neurons, causing changes in axonal morphology, although CBE has no effect on dendrite development. Co-incubation with CBE and inhibitors of sphingolipid synthesis such as fumonisin B1, an inhibitor of acylation of sphingoid long-chain bases, antagonizes the effects of CBE.5

    References:
    1. G. Grabowski et al. “Gaucher disease types 1, 2, and 3: differential mutations of the acid beta-glucosidase active site identified with conduritol B epoxide derivatives and sphingosine” Am J Hum Genet., Vol. 37 pp. 499-510, 1985
    2. S. Yang et al. “Inactivation of alpha-glucosidase by the active-site-directed inhibitor, conduritol B epoxide” Biochim Biophys Acta, Vol. 828(3) pp. 236- 240, 1985
    3. L. Premkumar et al. “X-ray Structure of Human Acid-beta-Glucosidase Covalently Bound to Conduritol-B-Epoxide Implications for Gaucher Disease” The Journal of Biological Chemistry, Vol. 280(25) pp. 23815-23819, 2005
    4. G. Grabowski et al. “Human acid beta-glucosidase. Use of conduritol B epoxide derivatives to investigate the catalytically active normal and Gaucher disease enzymes” The Journal of Biological Chemistry, Vol. 261(18) pp. 8263-8269, 1986
    5. E. Korkotian et al. “Elevation of Intracellular Glucosylceramide Levels Results in an Increase in Endoplasmic Reticulum Density and in Functional Calcium Stores in Cultured Neurons” The Journal of Biological Chemistry, Vol. 274(31) pp. 21673-21678, 1999