Abstract
An efficient method has been developed for the chemoselective cysteine modification of unprotected peptides and proteins in aqueous media through the formation of a vinyl sulfide linkage by using electron-deficient alkynes, including alkynoic amides, esters and alkynones. The terminal alkynone-modified peptides could be converted back into the unmodified peptides (81 % isolated yield) by adding thiols under mild conditions. The usefulness of this thiol-assisted cleavage of the vinyl sulfide linkage in peptides has been exemplified by the enrichment of a cysteine-containing peptide (71% recovery) from a mixture of cysteine-containing and non-cysteine-containing peptides. KGaA.
Original language | English |
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Pages (from-to) | 3839-3850 |
Number of pages | 12 |
Journal | Chemistry - A European Journal |
Volume | 15 |
Issue number | 15 |
DOIs | |
Publication status | Published - 6 Apr 2009 |
Externally published | Yes |
Keywords
- Alkynes
- Chemoselectivity
- Cleavage reactions
- Cysteine
- Peptides
ASJC Scopus subject areas
- Chemistry(all)