缺电子炔烃作为在水介质中修饰含半胱氨酸肽的可裂解试剂。
Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containing peptides in aqueous medium.
作者信息
Shiu Hoi-Yan, Chan Tak-Chung, Ho Chi-Ming, Liu Yungen, Wong Man-Kin, Che Chi-Ming
机构信息
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.
出版信息
Chemistry. 2009;15(15):3839-50. doi: 10.1002/chem.200800669.
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.
已开发出一种高效方法，通过使用缺电子炔烃（包括炔酰胺、酯和炔酮）形成乙烯基硫醚键，在水性介质中对未保护的肽和蛋白质进行化学选择性半胱氨酸修饰。在温和条件下添加硫醇，末端炔酮修饰的肽可转化回未修饰的肽（分离产率81%）。从含半胱氨酸和不含半胱氨酸的肽混合物中富集含半胱氨酸的肽（回收率71%），例证了这种硫醇辅助裂解肽中乙烯基硫醚键的实用性。
Zotero 插件