1160626-07-2Relevant academic research and scientific papers
Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containlng peptides in aqueous medium
Shiu, Hoi-Yan,Chan, Tak-Chung,Ho, Chi-Ming,Liu, Yungen,Wong, Man-Kin,Che, Chi-Ming
experimental part, p. 3839 - 3850 (2009/12/31)
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.
