Ontology highlight
ABSTRACT:
SUBMITTER: Crich D
PROVIDER: S-EPMC4658652 | biostudies-literature | 2006 Mar
REPOSITORIES: biostudies-literature
Crich David D Krishnamurthy Venkataramanan V Hutton Thomas K TK
Journal of the American Chemical Society 20060301 8
Alkylation of potassium selenosulfate with allylic halides gives Se-allyl seleno Bunte salts. On reaction with thiols at room temperature, these afford mixed dialkyl selenosulfides, which undergo 2,3-sigmatropic rearrangement with loss of selenium, either spontaneously or with assistance by triphenylphosphine, thereby providing mixed dialkyl sulfides and a new permanent chemical ligation method. The process is illustrated through the lipidation of cysteine-containing tripeptides and by the allyl ...[more]