title: Allylation and Alkylation of Biologically Relevant Nucleophiles by Diallyl Sulfides.
abstract: Allyl sulfides are bioactive phytochemicals found in garlic, onion, and other members of the genus Allium. Here we showed that diallyl disulfide and diallyl trisulfide can transfer allyl side chains to low molecular weight thiols. Diallyl monosulfide is inert with respect to this allyl transfer reaction. On the other hand, diallyl sulfone, a known metabolite of diallyl monosulfide, alkylates both amines and thiols under physiologically relevant conditions via isomerization to an electrophilic vinyl sulfone.
authors.affiliation: Department of Chemistry, University of Missouri , 125 Chemistry Building, Missouri 65211, United States.
authors.forename: Kasi
authors.initials: K
authors.lastname: Viswanatharaju Ruddraraju
authors.affiliation: Department of Chemistry, University of Missouri , 125 Chemistry Building, Missouri 65211, United States.
authors.forename: Zachary D
authors.initials: ZD
authors.lastname: Parsons
authors.affiliation: Department of Chemistry, University of Missouri , 125 Chemistry Building, Missouri 65211, United States.
authors.forename: Calvin D
authors.initials: CD
authors.lastname: Lewis
authors.affiliation: Department of Chemistry, University of Missouri , 125 Chemistry Building, Missouri 65211, United States.|Department of Biochemistry, University of Missouri , 125 Chemistry Building, Columbia, Missouri 65211, United States.
authors.forename: Kent S
authors.identifier: 0000-0002-4218-7411
authors.initials: KS
authors.lastname: Gates
mesh_terms: D000478:Alkylation; D000490:Allium / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry*; D015394:Molecular Structure; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D004220:Disulfides; D013440:Sulfides; C042577:diallyl trisulfide; C028009:diallyl disulfide; C038491:allyl sulfide