Synthesis of isothiocyanate-derived mercapturic acids.
Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables.
Vermeulen
Martijn
M
Department of Food and Food Supplement Analysis, TNO Nutrition and Food Research, P.O. Box 360, 3700 AJ, Zeist, The Netherlands. m.vermuelen@voeding.tno.nl
Zwanenburg
Binne
B
Chittenden
Gordon J F
GJ
Verhagen
Hans
H
D000111:Acetylcysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000652:urine; D015415:Biomarkers / Q000652:urine; D002851:Chromatography, High Pressure Liquid; D004032:Diet; D005961:Glucosinolates / Q000737:chemistry; D006801:Humans; D017879:Isothiocyanates / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013861:Thiocyanates / Q000378:metabolism / Q000652:urine; D014675:Vegetables / Q000737:chemistry / Q000378:metabolism
D015415:Biomarkers; D005961:Glucosinolates; D017879:Isothiocyanates; D013861:Thiocyanates; D000111:Acetylcysteine