Rapid Additive-Free Selenocystine鈥揝elenoester Peptide Ligation
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- 作者：Nicholas J. Mitchell ; Lara R. Malins ; Xuyu Liu ; Robert E. Thompson ; Bun Chan ; Leo Radom ; Richard J. Payne
- 刊名：Journal of the American Chemical Society
- 出版年：2015
- 出版时间：November 11, 2015
- 年：2015
- 卷：137
- 期：44
- 页码：14011-14014
- 全文大小：337K
- ISSN：1520-5126
文摘
We describe an unprecedented reaction between peptide selenoesters and peptide dimers bearing N-terminal selenocystine that proceeds in aqueous buffer to afford native amide bonds without the use of additives. The selenocystine-selenoester ligations are complete in minutes, even at sterically hindered junctions, and can be used in concert with one-pot deselenization chemistry. Various pathways for the transformation are proposed and probed through a combination of experimental and computational studies. Our new reaction manifold is also showcased in the total synthesis of two proteins.