Synthesis of 5-Cyano-Tryptophan as a Two-Dimensional Infrared Spectroscopic Reporter of Structure
| Autor: | Andrew J. Schmitz, Farzaneh Chalyavi, Michael W. Fennie, Philip H. Gilmartin, Matthew J. Tucker |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Materials science Spectral signature Nitrile Infrared Tryptophan Infrared spectroscopy Peptide General Medicine 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Crystallography chemistry 0210 nano-technology Peptide sequence Magnetic dipole–dipole interaction |
| Zdroj: | Angewandte Chemie International Edition. 57:7528-7532 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201803849 |
| Popis: | A concise synthesis of protected 5-cyano-l-tryptophan (Trp5CN ) has been developed for 2D IR spectroscopic investigations within either peptides or proteins. To assess the potential of differently substituted cyano-tryptophans, several model cyano-indole systems were characterized using IR spectroscopy. Upon assessment of their spectroscopic properties, Trp5CN was integrated into a model peptide sequence, Trp5CN -Gly-Phe4CN , to elucidate its structure. This peptide demonstrates the capability of this probe to capture structural information by 2D IR spectroscopy. The 2D IR spectrum of the peptide in water was simulated to reveal a unique spectral signature resulting from the presence of dipolar coupling. The coupling strength between cyano labels was determined to be 1.4 cm-1 by matching the slopes along the max contour for the simulated and experimental spectrum. Using transition dipole coupling, a distance between the two probes of 13 A was calculated. |
| Databáze: | OpenAIRE |
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