Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols.
J Am Chem Soc
; 128(8): 2544-5, 2006 Mar 01.
Article
em En
| MEDLINE
| ID: mdl-16492032
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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Oligopeptídeos
/
Compostos de Sulfidrila
/
Sulfetos
/
Compostos de Selênio
/
Cisteína
/
Compostos Alílicos
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2006
Tipo de documento:
Article
País de afiliação:
Estados Unidos