Names | |
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Preferred IUPAC name
(1S,2R,3S,4R,5R,6S)-5-(Hydroxymethyl)-7-oxabicyclo[4.1.0]heptane-2,3,4-triol | |
Other names
Cyclophellitol
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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Properties | |
Chemical formula
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C7H12O5 |
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 ?)
Infobox references
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Cyclophellitol is a potent irreversible inhibitor of beta-glucosidases.[1] 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.[2] 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.[1] The first total chemical synthesis of cyclophellitol was demonstrated by Tatsuta et al.[3] Synthetic derivatives of cyclophellitol have been used for the detection of enzymes such as glucocerebrosidase, deficiency of which results in Gaucher's disease.[4]