Palladium Oxidative Addition Complexes for Peptide and Protein Cross-linking.
TLDR
The proposed palladium oxidative addition complexes 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.Abstract:
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.read more
Citations
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Contemporary approaches to site-selective protein modification
Emily A. Hoyt,Pedro M. S. D. Cal,Bruno L. Oliveira,Bruno L. Oliveira,Gonçalo J. L. Bernardes,Gonçalo J. L. Bernardes +5 more
TL;DR: The goal of this Review is to provide a window through which to view the many opportunities created by novel protein modification techniques‚ and to act as an initial guide to help scientists find direction and form ideas in an ever-growing field.
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Late-Stage Peptide Diversification by Position-Selective C-H Activation.
TL;DR: Recent progress in organometallic C-H activation on peptides until June 2018 is summarized, including position- and chemoselective palladium-, ruthenium-, and manganese-catalyzed processes.
Journal ArticleDOI
Arylation Chemistry for Bioconjugation.
Chi Zhang,Ekaterina V. Vinogradova,Ekaterina V. Vinogradova,Alexander M. Spokoyny,Alexander M. Spokoyny,Stephen L. Buchwald,Bradley L. Pentelute +6 more
TL;DR: Sulfur, nitrogen, selenium, oxygen, and carbon arylative bioconjugation strategies and their applications to modify peptides, proteins, sugars, and nucleic acids are outlined and reviewed.
Journal ArticleDOI
Organometallic Gold(III) Reagents for Cysteine Arylation.
Marco S. Messina,Julia M. Stauber,Mary A. Waddington,Arnold L. Rheingold,Heather D. Maynard,Alexander M. Spokoyny +5 more
TL;DR: The selective and efficient arylation procedures presented in this work broaden the synthetic scope of cysteine bioconjugation and serve as promising routes for the modification of complex biomolecules.
Journal ArticleDOI
Late-Stage Diversification through Manganese-Catalyzed C-H Activation: Access to Acyclic, Hybrid, and Stapled Peptides.
TL;DR: The unique robustness of the manganese(I) catalysis manifold was reflected by full tolerance of sensitive functional groups, such as iodides, esters, amides, and OH-free hydroxy groups, thereby setting the stage for the racemization-free synthesis of C-H fused peptide hybrids featuring steroids, drug molecules, natural products, nucleobases, and saccharides.
References
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TL;DR: The utility of each endogenous amino acid-selective conjugation methodology in the fields of biology and protein science has been surveyed with emphasis on the most relevant among reported transformations.
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A Perfluoroaryl-Cysteine SNAr Chemistry Approach to Unprotected Peptide Stapling
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Organometallic palladium reagents for cysteine bioconjugation
Ekaterina V. Vinogradova,Chi Zhang,Alexander M. Spokoyny,Bradley L. Pentelute,Stephen L. Buchwald +4 more
TL;DR: It is reported that palladium(ii) complexes can be used for efficient and highly selective cysteine conjugation (bioconjugation) reactions that are rapid and robust under a range of bio-compatible reaction conditions.