| dbo:abstract |
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. (en) |
| dbo:alternativeName |
Cyclophellitol (en) |
| dbo:iupacName |
(1S,2R,3S,4R,5R,6S)-5-(Hydroxymethyl)-7-oxabicyclo[4.1.0]heptane-2,3,4-triol (en) |
| dbo:thumbnail |
wiki-commons:Special:FilePath/Cyclophellitol.png?width=300 |
| dbo:wikiPageID |
63805391 (xsd:integer) |
| dbo:wikiPageLength |
3173 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID |
1022300179 (xsd:integer) |
| dbo:wikiPageWikiLink |
dbr:Enzyme_inhibitor dbr:Epoxide dbr:Beta-glucosidase dbr:Cyclitol dbc:Cyclitols dbr:Ester dbr:Nucleophile dbr:Gaucher's_disease dbr:Glucose dbr:Addition_reaction dbr:Acetal dbr:Glucocerebrosidase dbr:Glucoside dbr:Glycoside_hydrolase dbr:Japan dbr:Phellinus dbr:Irreversible_inhibitor |
| dbp:imagefile |
Cyclophellitol.png (en) |
| dbp:imagesize |
200 (xsd:integer) |
| dbp:othernames |
Cyclophellitol (en) |
| dbp:pin |
-5 (xsd:integer) |
| dbp:verifiedfields |
changed (en) |
| dbp:watchedfields |
changed (en) |
| dbp:wikiPageUsesTemplate |
dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Reflist dbt:Cascite dbt:Chemspidercite dbt:Stdinchicite |
| dcterms:subject |
dbc:Cyclitols |
| rdf:type |
owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 dbo:ChemicalCompound |
| rdfs:comment |
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. (en) |
| rdfs:label |
Cyclophellitol (en) |
| owl:sameAs |
wikidata:Cyclophellitol https://global.dbpedia.org/id/BASfv |
| prov:wasDerivedFrom |
wikipedia-en:Cyclophellitol?oldid=1022300179&ns=0 |
| foaf:depiction |
wiki-commons:Special:FilePath/Cyclophellitol.png |
| foaf:isPrimaryTopicOf |
wikipedia-en:Cyclophellitol |
| is dbo:wikiPageWikiLink of |
dbr:C7H12O5 |
| is foaf:primaryTopic of |
wikipedia-en:Cyclophellitol |
