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Electrostatic Control of Peptide Side-Chain Reactivity Using Amphiphilic Homopolymer-Based Supramolecular Assemblies

Electrostatic Control of Peptide Side-Chain Reactivity Using Amphiphilic Homopolymer-Based Supramolecular Assemblies

Feng Wang, Andrea Gomez-Escudero, Rajasekhar R Ramireddy, Gladys Murage, S Thayumanavan, Richard W Vachet

J Am Chem Soc. 2013 Sep 25;135(38):14179-88.

PMID: 23971726

Abstract:

Supramolecular assemblies formed by amphiphilic homopolymers with negatively charged groups in the hydrophilic segment have been designed to enable high labeling selectivity toward reactive side chain functional groups in peptides. The negatively charged interiors of the supramolecular assemblies are found to block the reactivity of protonated amines that would otherwise be reactive in aqueous solution, while maintaining the reactivity of nonprotonated amines. Simple changes to the pH of the assemblies' interiors allow control over the reactivity of different functional groups in a manner that is dependent on the pKa of a given peptide functional group. The labeling studies carried out in positively charged supramolecular assemblies and free buffer solution show that, even when the amine is protonated, labeling selectivity exists only when complementary electrostatic interactions are present, thereby demonstrating the electrostatically controlled nature of these reactions.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42412861	PSTAIRE peptide			Price

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