AI Article Synopsis
- Alkylation of potassium selenosulfate with allylic halides results in the creation of Se-allyl seleno Bunte salts.
- Upon reacting these salts with thiols at room temperature, mixed dialkyl selenosulfides are produced, which can undergo a rearrangement that involves losing selenium.
- This reaction can lead to the formation of mixed dialkyl sulfides and introduces a new method for permanent chemical ligation, demonstrated in applications involving cysteine-containing tripeptides and 1-thioglucose tetraacetate.
Article Abstract
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 allylation of 1-thioglucose tetraacetate.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4658652 | PMC |
| http://dx.doi.org/10.1021/ja057521c | DOI Listing |
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