Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: a chemoenzymatic route to sulforaphane.
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.
Iori
R
R
Istituto Sperimentale per le Colture Industriali, MiPA, Bologna, Italy. istsci6@iperbole.bologna.it
Bernardi
R
R
Gueyrard
D
D
Rollin
P
P
Palmieri
S
S
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*
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