期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 15, 页码 3839-3850出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800669
关键词
alkynes; chemoselectivity; cleavage reactions; cysteine; peptides
资金
- The University of Hong Kong
- Area of Excellence Scheme [AoE/P-10-01]
- Research Grants Council (HKSAR) [HKU 7052/07P]
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.
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