title: Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: a chemoenzymatic route to sulforaphane.
abstract: A new semi-synthetic way to produce glucoraphanin (2), the bio-precursor of the potential anticarcinogen sulforaphane (3), has been developed. Starting from glucoerucin (1), isolated from ripe seeds of Eruca sativa, glucoraphanin was obtained through chemoselective oxidation. Controlled myrosinase-catalysed hydrolysis of this precursor quantitatively afforded sulforaphane.
authors.affiliation: Istituto Sperimentale per le Colture Industriali, MiPA, Bologna, Italy. istsci6@iperbole.bologna.it
authors.forename: R
authors.initials: R
authors.lastname: Iori
authors.forename: R
authors.initials: R
authors.lastname: Bernardi
authors.forename: D
authors.initials: D
authors.lastname: Gueyrard
authors.forename: P
authors.initials: P
authors.lastname: Rollin
authors.forename: S
authors.initials: S
authors.lastname: Palmieri
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005961:Glucosinolates; D006026:Glycoside Hydrolases / Q000737:chemistry*; D007096:Imidoesters / Q000138:chemical synthesis* / Q000737:chemistry*; D017879:Isothiocyanates; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010091:Oximes; D013454:Sulfoxides; D013861:Thiocyanates / Q000138:chemical synthesis*
chemical_list: D005961:Glucosinolates; D007096:Imidoesters; D017879:Isothiocyanates; D010091:Oximes; D013454:Sulfoxides; D013861:Thiocyanates; C119493:glucoerucin; D006026:Glycoside Hydrolases; C022739:thioglucosidase; C016766:sulforaphane; D005947:Glucose; C119494:glucoraphanin