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Organometallic Gold(III) Reagents for Cysteine Arylation.

ABSTRACT: An efficient method for chemoselective cysteine arylation of unprotected peptides and proteins using Au(III) organometallic complexes is reported. The bioconjugation reactions proceed rapidly (<5 min) at ambient temperature in various buffers and within a wide pH range (0.5-14). This approach provides access to a diverse array of S-aryl bioconjugates including fluorescent dye, complex drug molecule, affinity label, poly(ethylene glycol) tags, and a stapled peptide. A library of Au(III) arylation reagents can be prepared as air-stable, crystalline solids in one step from commercial reagents. 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.

SUBMITTER: Messina MS

PROVIDER: S-EPMC6491213 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Organometallic Gold(III) Reagents for Cysteine Arylation.

Messina Marco S MS Stauber Julia M JM Waddington Mary A MA Rheingold Arnold L AL Maynard Heather D HD Spokoyny Alexander M AM

Journal of the American Chemical Society 20180530 23

An efficient method for chemoselective cysteine arylation of unprotected peptides and proteins using Au(III) organometallic complexes is reported. The bioconjugation reactions proceed rapidly (<5 min) at ambient temperature in various buffers and within a wide pH range (0.5-14). This approach provides access to a diverse array of S-aryl bioconjugates including fluorescent dye, complex drug molecule, affinity label, poly(ethylene glycol) tags, and a stapled peptide. A library of Au(III) arylation ...[more]

PMID: 29790740

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