ArticlePhysical chemistry chemical physics : PCCP2016
C≡N stretching vibration of 5-cyanotryptophan as an infrared probe of protein local environment: what determines its frequency?
Article in Physical chemistry chemical physics : PCCP, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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23 citing papers in PubMed, 64 citations in OpenAlex.
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- Investigation of the Vibrational Characteristics of 6-Isocyano-1-Methyl-1H-Indole: Utilizing the Isonitrile Group as an Infrared Probe.Molecules (Basel, Switzerland) · 2023Article
- Good Vibrations Report on the DNA Quadruplex Binding of an Excited State Amplified Ruthenium Polypyridyl IR Probe.Journal of the American Chemical Society · 2023Article
- IR linewidth and intensity amplifications of nitrile vibrations report nuclear-electronic couplings and associated structural heterogeneity in radical anions.Chemical science · 2021Article
- Vibrational Spectroscopic Map, Vibrational Spectroscopy, and Intermolecular Interaction.Chemical reviews · 2020Review
- Tuning Molecular Vibrational Energy Flow within an Aromatic Scaffold via Anharmonic Coupling.The journal of physical chemistry. A · 2019Article
- Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments.Molecules (Basel, Switzerland) · 2019Article
- 4-Cyanoindole-2'-deoxyribonucleoside as a Dual Fluorescence and Infrared Probe of DNA Structure and Dynamics.Molecules (Basel, Switzerland) · 2019Article
- Probe of Alcohol Structures in the Gas and Liquid States Using C⁻H Stretching Raman Spectroscopy.Sensors (Basel, Switzerland) · 2018Review
- 7-Cyanoindole fluorescence as a local hydration reporter: application to probe the microheterogeneity of nine water-organic binary mixtures.Physical chemistry chemical physics : PCCP · 2018Article
- Electrons dynamics control by shaping femtosecond laser pulses in micro/nanofabrication: modeling, method, measurement and application.Light, science & applications · 2018Review
- Solvent Dependence of Cyanoindole Fluorescence Lifetime.Chemical physics letters · 2017Article
- Watching Proteins Wiggle: Mapping Structures with Two-Dimensional Infrared Spectroscopy.Chemical reviews · 2017Review
- Fermi resonance as a means to determine the hydrogen-bonding status of two infrared probes.Physical chemistry chemical physics : PCCP · 2017Article
- Do guanidinium and tetrapropylammonium ions specifically interact with aromatic amino acid side chains?Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Infrared and fluorescence assessment of the hydration status of the tryptophan gate in the influenza A M2 proton channel.Physical chemistry chemical physics : PCCP · 2016Article
- Minimalist IR and fluorescence probes of protein function.Current opinion in chemical biology · 2016Review
- Two-Dimensional Infrared Study of Vibrational Coupling between Azide and Nitrile Reporters in a RNA Nucleoside.The journal of physical chemistry. B · 2016Article
- Exciton circular dichroism couplet arising from nitrile-derivatized aromatic residues as a structural probe of proteins.Analytical biochemistry · 2016Article
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Authors and funding
5 authors at 4 institutions in 2 countries.
Funding
Abstract
Recently it has been suggested that the C≡N stretching vibration of a tryptophan analog, 5-cyanotryptophan, could be used as an infrared probe of the local environment, especially the hydration status, of tryptophan residues in proteins. However, the factors that influence the frequency of this vibrational mode are not understood. To determine these factors, herein we carried out linear and nonlinear infrared measurements on the C≡N stretching vibration of the sidechain of 5-cyanotryptophan, 3-methyl-5-cyanoindole, in a series of protic and aprotic solvents. We found that while the C≡N stretching frequencies obtained in these solvents do not correlate well with any individual Kamlet-Taft solvent parameter, i.e., π* (polarizability), β (hydrogen bond accepting ability), and α (hydrogen bond donating ability), they do however, collapse on a straight line when plotted against σ = π* + β - α. This linear relationship provides a firm indication that both specific interactions, i.e., hydrogen-bonding interactions with the C≡N (through α) and indole N-H (through β) groups, and non-specific interactions with the molecule (through π*) work together to determine the C≡N stretching frequency, thus laying a quantitative framework for applying 5-cyanotryptophan to investigate the microscopic environment of proteins in a site-specific manner. Furthermore, two-dimensional and pump-probe infrared measurements revealed that a significant portion (∼31%) of the ground state bleach signal has a decay time constant of ∼12.3 ps, due to an additional vibrational relaxation channel, making it possible to use 5-cyanotryptophan to probe dynamics occurring on a timescale on the order of tens of picoseconds.
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