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The free-radical hydrothiolation of alkynes (thiol-yne coupling, TYC) unites two thiol fragments across the carbon-carbon triple bond to give a dithioether derivative with exclusive 1,2-addition; this reaction can be used for modification of peptides and proteins allowing glycoconjugation and fluorescent labeling. These results have implications not only as a flexible strategy for attaching two modifications at a single site in proteins but also for unanticipated side-reactions of reagents (such as cycloalkynes) used in other protein coupling reactions.

Original publication

DOI

10.1039/c1cc14402b

Type

Journal article

Journal

Chem Commun (Camb)

Publication Date

21/10/2011

Volume

47

Pages

11086 - 11088

Keywords

Alkynes, Animals, Cattle, Models, Molecular, Protein Conformation, Serum Albumin, Bovine, Sulfhydryl Compounds