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Electron‐Deficient Alkynes as Cleavable Reagents for the Modification of Cysteine‐Containing Peptides in Aqueous Medium
Author(s) -
Shiu HoiYan,
Chan TakChung,
Ho ChiMing,
Liu Yungen,
Wong ManKin,
Che ChiMing
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800669
Subject(s) - cysteine , chemistry , reagent , peptide , sulfide , combinatorial chemistry , cleavage (geology) , aqueous medium , thiol , aqueous solution , peptide synthesis , organic chemistry , yield (engineering) , biochemistry , enzyme , materials science , fracture (geology) , composite material , metallurgy
Abstract Enriched cleavage : 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.