Palladium Oxidative Addition Complexes for Peptide and Protein Cross-linking

被引:84
|
作者
Kubota, Koji [1 ]
Dai, Peng [1 ]
Pentelute, Bradley L. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院; 日本学术振兴会;
关键词
NONCANONICAL AMINO-ACIDS; UNPROTECTED PEPTIDES; STAPLED PEPTIDES; MACROCYCLIZATION; ARYLATION; BIOCONJUGATION; DESIGN; CHAINS;
D O I
10.1021/jacs.8b00172
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for cysteine lysine cross-linking in peptides and proteins using palladium oxidative addition complexes is presented. First, a biarylphosphine-supported palladium reagent is used to transfer an aryl group bearing an O-phenyl carbamate substituent to a cysteine residue. Next, this carbamate undergoes chemoselective acyl substitution by a proximal lysine to form a cross-link. The linkage so formed is stable toward acid, base, oxygen, and external thiol nucleophiles. This method was applied to cross-link cysteine with nearby lysines in sortase A*. Furthermore, we used this method for the intermolecular cross-linking between a peptide and a protein based on the p53-MDM2 interaction. These studies demonstrate the potential for palladium-mediated methods to serve as a platform for the development of future cross-linking techniques for peptides and proteins with natural amino acid residues.
引用
收藏
页码:3128 / 3133
页数:6
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