Crich David, Krishnamurthy Venkataramanan, Hutton Thomas K
Department of Chemistry, University of Illinois at Chicago, 60607-7061, USA.
J Am Chem Soc. 2006 Mar 1;128(8):2544-5. doi: 10.1021/ja057521c.
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.
亚硒酸钾硫酸酯与烯丙基卤进行烷基化反应可生成硒代烯丙基硒代邦特盐。在室温下与硫醇反应时,这些盐会生成混合二烷基硒代硫化物,其会自发地或在三苯基膦的协助下发生2,3 - 西格玛重排并失去硒,从而得到混合二烷基硫化物以及一种新的永久性化学连接方法。该过程通过含半胱氨酸三肽的脂化反应以及1 - 硫代葡萄糖四乙酸酯的烯丙基化反应得以说明。