Cyclophellitol

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.

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Cyclophellitol

Names
Preferred IUPAC name (1S,2R,3S,4R,5R,6S)-5-(Hydroxymethyl)-7-oxabicyclo[4.1.0]heptane-2,3,4-triol
Other names Cyclophellitol
Identifiers
CAS Number	126661-83-4 Y[PubChem]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL35576
ChemSpider	144010 Y
PubChem CID	164227
CompTox Dashboard (EPA)	DTXSID80925661
InChI InChI=1S/C7H12O5/c8-1-2-3(9)4(10)5(11)7-6(2)12-7/h2-11H,1H2/t2-,3-,4+,5-,6-,7+/m1/s1 Y Key: YQLWKYQDOQEWRD-GEGSFZHJSA-N Y InChI=1S/C7H12O5/c8-1-2-3(9)4(10)5(11)7-6(2)12-7/h2-11H,1H2/t2-,3-,4+,5-,6-,7+/m1/s1 Key: YQLWKYQDOQEWRD-GEGSFZHJSA-N
SMILES C([C@@H]1[C@H]([C@@H]([C@H]([C@H]2[C@@H]1O2)O)O)O)O
Properties
Chemical formula	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). N (what is YN ?) Infobox references

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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]