Improving the fluorescent probe acridonylalanine through a combination of theory and experiment
| Autor: | Rahul M. Kohli, George A. Petersson, Anand K. Muthusamy, Naoya Ieda, Taylor M. Barrett, Zachary M Hostetler, Joomyung V. Jun, Chunxiao Liu, E. James Petersson, Itthipol Sungwienwong, Amara Hendricks, John J. Ferrie, David M. Chenoweth |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Fluorophore 010405 organic chemistry Aminoacyl tRNA synthetase Organic Chemistry food and beverages 010402 general chemistry 01 natural sciences Fluorescence Combinatorial chemistry Acceptor Article Fluorescence spectroscopy 0104 chemical sciences Amino acid chemistry.chemical_compound Förster resonance energy transfer chemistry Peptide synthesis Physical and Theoretical Chemistry |
| Zdroj: | Journal of Physical Organic Chemistry. 31 |
| ISSN: | 1099-1395 0894-3230 |
| Popis: | Acridonylalanine (Acd) is a useful fluorophore for studying proteins by fluorescence spectroscopy, but it can potentially be improved by being made longer wavelength or brighter. Here, we report the synthesis of Acd core derivatives and their photophysical characterization. We also performed ab initio calculations of the absorption and emission spectra of Acd derivatives, which agree well with experimental measurements. The amino acid aminoacridonylalanine (Aad) was synthesized in forms appropriate for genetic incorporation and peptide synthesis. We show that Aad is a superior Förster resonance energy transfer acceptor to Acd in a peptide cleavage assay and that Aad can be activated by an aminoacyl tRNA synthetase for genetic incorporation. Together, these results show that we can use computation to design enhanced Acd derivatives, which can be used in peptides and proteins. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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