TY - JOUR
T1 - Allylation and Alkylation of Biologically Relevant Nucleophiles by Diallyl Sulfides
AU - Viswanatharaju Ruddraraju, Kasi
AU - Parsons, Zachary D.
AU - Lewis, Calvin D.
AU - Gates, Kent S.
N1 - Funding Information:
This was made possible in part by Grant Number P50AT006273 from the National Center for Complementary and Alternative Medicines (NCCAM), the Office of Dietary Supplements (ODS), and the National Cancer Institute (NCI). Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the NCCAM, ODS, NCI, or the National Institutes of Health.
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2017/1/6
Y1 - 2017/1/6
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/85018523735
U2 - 10.1021/acs.joc.6b02517
DO - 10.1021/acs.joc.6b02517
M3 - Article
C2 - 27973787
AN - SCOPUS:85018523735
SN - 0022-3263
VL - 82
SP - 776
EP - 780
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -