Influence of a substituent on amide nitrogen atom on fluorescence efficiency quenching of Tyr(Me) by amide group

Łukomska, Joanna; Rzeska, Alicja; Malicka, Joanna; Wiczk, Wiesław

doi:10.1016/s1010-6030(01)00521-4

Cited by 15 publications

(14 citation statements)

References 23 publications

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“…3 The methylation of the hydroxyl group of the phenolic ring of tyrosine increases both the fluorescence quantum yield and the fluorescence lifetime, in comparison to those of tyrosine, but it does not change the character of the fluorescence intensity decay of tyrosine itself, its amide, or its N-acetyl derivatives. 3,14 The photophysical properties of buried tyrosine residues in proteins are different than those of tyrosine that has been exposed to the solvent. 23 They also undergo substantial changes while the protein folds from a random coil to a globular structure.…”

Section: Introductionmentioning

confidence: 99%

Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations

et al. 2004

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The photophysical properties of tyrosine and its derivatives with free and blocked functional groups in water were studied by steady-state and time-resolved fluorescence spectroscopy and global analysis. Tyrosine fluorescence intensity decays in water at pH ) 5.5 in the short-wavelength region (290-320 nm) are monoexponential, whereas, at longer wavelengths, they are biexponential. The monoexponential fluorescence intensity decay of O-methyl tyrosine across the fluorescence band is observed. The fluorescence lifetimes of Tyr calculated using a global analysis are equal to 3.37 ( 0.04 ns at the short-wavelength region and 0.98 ( 0.12 ns at the longer-wavelength region. This observation, together with the decay-associated spectra, indicate that the short-lifetime component can be attributed to tyrosine with phenol hydroxyl groups hydrogen-bonded with water molecules. The rotamer populations calculated from potentials of mean forces, as well as those obtained from 1 H NMR spectroscopy, do not correspond to the pre-exponential factors obtained from fluorescence spectroscopy. The calculated energy barriers of rotations about the C R -C β bond indicate that the interconversion rate constant for tyrosine and N-acetyl-tyrosinamide are much greater than the fluorescence rate constant. Monoexponential fluorescence intensity decay of tyrosine derivatives in acetonitrile solution is observed for all derivatives studied and, contrary to the aqueous solution, the amide group does not quench the fluorescence. Thus, specific conformation(s) stabilized by the hydrogen-bond network seem to be responsible for the heterogeneous fluorescence intensity decay of tyrosine derivatives in aqueous solution.

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Section: Introductionmentioning

confidence: 99%

Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations

et al. 2004

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“…For AcTyrNH 2 in all solvents studied monoexponential fluorescence decays were observed, and the fluorescence lifetimes obtained in MeOH and DMSO are comparable to published results (26). For O ‐methyl‐tyrosine and its derivatives with free or with one or both functional groups blocked, the fluorescence decays are mono‐exponential in all studied solvents, whereas in water solution the quenching of Tyr(Me) fluorescence by amide group is observed (7, 9, 15).…”

Section: Resultsmentioning

confidence: 96%

“…The different lifetimes of the rotamers arise from the interaction between the phenol fluorophore and the quenching groups. A charge transfer interaction between the excited aromatic chromophore (phenol ring) as a donor and the electrophilic units in the amino acid backbone (the carbonyl of the amide group) as an acceptor was proposed by Cowgill (31,32), Toumon et al (33) and Feitelson (10) and confirmed by others (7,9,24,26). The slow-exchange ground state rotamer model in the case of tyrosine derivatives predicts that the fluorescence intensity decay should be described by the sum of three exponents; this in which the phenol ring comes into the closest contact with the carbonyl group has the shortest fluorescence lifetime.…”

Section: Introductionmentioning

confidence: 79%

“…In the case of the tyrosine zwitterion and tyrosine derivatives with an ionized α‐carboxyl group, mono‐exponential fluorescence decays were observed (3–8). The conversion of the α‐carboxyl group into the corresponding amide or its protonation results in a complex fluorescence decay (1–26). An explanation of this behaviour was offered by the Gauduchon and Wahl ground state rotamer model (6).…”

Section: Introductionmentioning

confidence: 99%

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Photophysical Properties of Tyrosine and Its Simple Derivatives in Organic Solvents Studied by Time‐resolved Fluorescence Spectroscopy and Global Analysis^¶

Guzow

Rzeska

Mrozek

et al. 2005

Photochem & Photobiology

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Photophysical properties of tyrosine and its derivatives with free and blocked functional groups were studied by steady state and time‐resolved fluorescence spectroscopy and global analysis in organic solvents, such as methanol, 2‐propanol, tetrahydrofuran (THF), and dimethylsulfoxide (DMSO). The mono‐exponential fluorescence intensity decays were observed for all tyrosine derivatives in THF and DMSO solutions, whereas in alcohols some derivatives have bi‐exponential decays. The rotamer population calculated from 1H nuclear magnetic resonance spectroscopy in DMSO does not correspond to the pre‐exponential factors obtained from fluorescence spectroscopy. Moreover in the case of DMSO, the strong interaction of this solvent with the hydroxyl group of the fluorophore's phenol ring causes substantial changes in the fluorescence and nonradiative rate constants of tyrosine derivatives compared with those of tyrosine with a blocked hydroxyl group, Tyr(Me). The steady state and time‐resolved fluorescence measurements in pure organic solvents and water‐organic solvent mixtures indicate that the fluorescence quenching of the phenol chromophore of tyrosine by an acetyl or amide group or both depends on the polarity of the solvent used as well as the ability of the solvent to form hydrogen bonds with functional groups of tyrosine.

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“…Tyrosine is one of the 20 amino acids commonly found in proteins. The photophysical properties of tyrosine and its derivatives are very complex and have been widely investigated [1][2][3][4][5][6]. The fluorescence of aromatic amino acids and their residues incorporated into a peptide or protein chain is the subject of extensive studies because of their use as internal probes in conformational analysis [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Surfactant and Temperature Effects in Tyrosine/Pyridoxine Hydrochloride Systems

Mote¹,

Anbhule

Kolekar

2016

J Surfact & Detergents

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The fluorescence resonance energy transfer (FRET) from tyrosine to pyridoxine hydrochloride in different surfactant solutions and in deionized water has been investigated by using a fluorescence spectroscopic technique. The Stern-Volmer quenching constant, the distance between donor (tyrosine) and acceptor (pyridoxine hydrochloride), and the energy transfer efficiency were obtained using the Stern-Volmer relation and Forster's theory of nonradiative energy transfer. The data obtained from the measurement reveals that the FRET occurs more effectively in aqueous SDS micellar solution than in CTAB or linear alcohol ethoxylate micellar systems and deionized water. Moreover, the binding constant, number of binding sites, and thermodynamic parameters DG, DH, DS were obtained by studying the tyrosine-pyridoxine hydrochloride interactions at three different temperatures. The decrease in binding constant with temperature reflects the existence of weak interaction between tyrosine and pyridoxine hydrochloride at high temperature. The analysis confirms that van der Waals forces and hydrogen bonding are involved in the interaction.

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Influence of a substituent on amide nitrogen atom on fluorescence efficiency quenching of Tyr(Me) by amide group

Cited by 15 publications

References 23 publications

Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations

Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations

Photophysical Properties of Tyrosine and Its Simple Derivatives in Organic Solvents Studied by Time‐resolved Fluorescence Spectroscopy and Global Analysis^¶

Surfactant and Temperature Effects in Tyrosine/Pyridoxine Hydrochloride Systems

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Influence of a substituent on amide nitrogen atom on fluorescence efficiency quenching of Tyr(Me) by amide group

Cited by 15 publications

References 23 publications

Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations

Photophysical Properties of Tyrosine and Its Simple Derivatives Studied by Time-Resolved Fluorescence Spectroscopy, Global Analysis, and Theoretical Calculations

Photophysical Properties of Tyrosine and Its Simple Derivatives in Organic Solvents Studied by Time‐resolved Fluorescence Spectroscopy and Global Analysis¶

Surfactant and Temperature Effects in Tyrosine/Pyridoxine Hydrochloride Systems

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Photophysical Properties of Tyrosine and Its Simple Derivatives in Organic Solvents Studied by Time‐resolved Fluorescence Spectroscopy and Global Analysis^¶