|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||176.168 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
what is ?)(
Cyclophellitol is a potent irreversible inhibitor of beta-glucosidases. It is a cyclitol mimic of beta-glucose with an epoxide group in place of the acetal group found in glucosides. When recognized, cyclophellitol undergoes an acid-catalyzed ring-opening addition reaction with the catalytic nucleophile of a retaining glycoside hydrolase. The resulting ester linkage cannot be hydrolyzed by the normal catalytic machinery of the enzyme, resulting in irreversible inhibition.
Cyclophellitol was originally isolated from a species of Phellinus mushroom found in Japan. The first total chemical synthesis of cyclophellitol was demonstrated by Tatsuta et al. Synthetic derivatives of cyclophellitol have been used for the detection of enzymes such as glucocerebrosidase, deficiency of which results in Gaucher's disease.
- Atsumi, S. et al. (1990) ‘Production, isolation and structure determination of a novel β-glucosidase Inhibitor, cyclophellitol, from phellinus sp’, The Journal of Antibiotics. Japan Antibiotics Research Association, 43(1), pp. 49–53. doi: 10.7164/antibiotics.43.49.
- Gloster, T. M., Madsen, R. and Davies, G. J. (2007) ‘Structural basis for cyclophellitol inhibition of a β-glucosidase’, Organic and Biomolecular Chemistry. The Royal Society of Chemistry, 5(3), pp. 444–446. doi: 10.1039/b616590g.
- Tatsuta, K. et al. (1991) ‘Syntheses and Enzyme Inhibiting Activities of Cyclophellitol Analogs’, Journal of Antibiotics. Japan Antibiotics Research Association, 44(8), pp. 912–914. doi: 10.7164/antibiotics.44.912.
- Witte, M. D. et al. (2010) ‘Ultrasensitive in situ visualization of active glucocerebrosidase molecules’, Nature Chemical Biology. Nature Publishing Group, 6(12), pp. 907–913. doi: 10.1038/nchembio.466.