Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containing peptides in aqueous medium.
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.
Shiu
Hoi-Yan
HY
Department of Chemistry and Open Laboratory of Chemical Biology, Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
Chan
Tak-Chung
TC
Ho
Chi-Ming
CM
Liu
Yungen
Y
Wong
Man-Kin
MK
Che
Chi-Ming
CM
D000418:Albumins / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry; D004583:Electrons; D008024:Ligands; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013440:Sulfides / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D000418:Albumins; D000480:Alkynes; D008024:Ligands; D010455:Peptides; D013438:Sulfhydryl Compounds; D013440:Sulfides; D014753:Vinyl Compounds; D003545:Cysteine