Rapid Additive-Free Selenocystine–Selenoester Peptide Ligation | Zendy

Nicholas J. Mitchell | Zendy; Lara R. Malins | Zendy; Xuyu Liu | Zendy; Robert E. Thompson | Zendy; Bun Chan | Zendy; Leo Radom | Zendy; Richard J. Payne | Zendy

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Rapid Additive-Free Selenocystine–Selenoester Peptide Ligation

Author(s) -

Nicholas J. Mitchell,

Lara R. Malins,

Xuyu Liu,

Robert E. Thompson,

Bun Chan,

Leo Radom,

Richard J. Payne

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b07237

Subject(s) - chemistry , steric effects , peptide , amide , combinatorial chemistry , aqueous solution , stereochemistry , organic chemistry , biochemistry

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.

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