Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 23, Pages 7065-7069Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b04115
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Funding
- UCLA Department of Chemistry and Biochemistry
- 3M
- Alfred P. Sloan Foundation
- National Institutes of Health (NIH) [R35GM124746]
- National Science Foundation (NSF) [CHE-1507735]
- NSF [HRD-1400789, DGE-0707424]
- UCLA
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM124746] Funding Source: NIH RePORTER
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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.
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