Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/17269
Title: Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containing peptides in aqueous medium
Authors: Shiu, HY
Chan, TC
Ho, CM
Liu, Y
Wong, MK 
Che, CM
Keywords: Alkynes
Chemoselectivity
Cleavage reactions
Cysteine
Peptides
Issue Date: 2009
Publisher: Wiley-VCH
Source: Chemistry - a European journal, 2009, v. 15, no. 15, p. 3839-3850 How to cite?
Journal: Chemistry - a European journal 
Abstract: An efficient chemoselective cysteine modification of unprotected peptides and proteins has been developed by using electron-deficient alkynes in aqueous media. Interestingly, terminal alkynone-modified peptides could be converted back into the unmodified peptides by cleavage by adding thiols under mild conditions (see scheme). 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.
URI: http://hdl.handle.net/10397/17269
ISSN: 0947-6539
EISSN: 1521-3765
DOI: 10.1002/chem.200800669
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