Allylation and Alkylation of Biologically Relevant Nucleophiles by Diallyl Sulfides.
Allylation and Alkylation of Biologically Relevant Nucleophiles by Diallyl Sulfides.
复制标题
DOI：
10.1021/acs.joc.6b02517
复制
发表时间：
2017-01
期刊：
影响因子：
--
通讯作者：
Kasi Viswanatharaju Ruddraraju;Zachary D. Parsons;Calvin D. Lewis;K. Gates
中科院分区：
文献类型：
--
作者：
Kasi Viswanatharaju Ruddraraju;Zachary D. Parsons;Calvin D. Lewis;K. Gates
烯丙基硫化物是在大蒜、洋葱和其他葱属植物中发现的生物活性植物化学物质。我们发现二烯丙基二硫和二烯丙基三硫可以将烯丙基侧链转移到低分子量的硫醇上。单硫二烯丙基在烯丙基转移反应中是惰性的。另一方面，二烯丙基砜，一种已知的二烯丙基单硫化物的代谢物，在生理相关条件下通过异构化反应将胺和硫醇烷基化成亲电的乙烯基砜。
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.