Journal
CHEMICAL COMMUNICATIONS
Volume 47, Issue 39, Pages 11086-11088Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1cc14402b
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Funding
- Fundacion Ramon Areces
- Royal Society
- BBSRC [BB/E004350/1] Funding Source: UKRI
- EPSRC [EP/G026688/1, EP/I500200/1, EP/E000614/1] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BB/E004350/1, BB/C510824/1, EGA17763] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/D023343/1, EP/G026688/1, EP/I500200/1, EP/D023335/1, GR/T26542/01, EP/E000614/1] Funding Source: researchfish
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The free-radical hydrothiolation of alkynes (thiol-yne dagger 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.
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