Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems
Abstract
:1. Introduction
2. Results and Discussions
2.1. NMR and CIDNP Study
2.2. Electron Dipole–Dipole Interaction as a Factor of the Chiral Centers’ Influence on CIDNP (Theoretical Part)
2.3. Fluorescence Measurement
2.4. Modern Concepts of the Mutual Influence of Chiral Centers
3. Materials and Methods
3.1. Synthesis
3.2. Optical Spectroscopy
3.3. NMR Measurements
3.4. Pseudo Steady-State Photo-CIDNP (PSS)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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K(CH2) | K(NH) | |
---|---|---|
(S,S) | 1.91 | 2.08 |
(S,R), (R,S) | 0.195 | 0.255 |
KSS/KSR,RS | 9.8 | 8.2 |
Average | 9.0 |
(R,S)-KP-Trp | (S,R)-KP-Trp | (S,S)-KP-Trp | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
ε | τ1, ns | A1, % | τ2, ns | A2, % | τ1, ns | A1, % | τ2, ns | A2, % | τ1, ns | A1, % | τ2, ns | A2, % |
36.8 | 0.2 ± 0.1 | 49 | 4.5 ± 0.5 | 51 | 0.1 ± 0.1 | 27 | 4.4 ± 0.4 | 73 | 0.1 ± 0.1 | 50 | 4.3 ± 0.4 | 50 |
30.25 | 0.2 ± 0.1 | 55 | 4.6 ± 0.5 | 45 | 0.2 ± 0.1 | 27 | 4.3 ± 0.4 | 73 | 0.1 ± 0.1 | 44 | 4.1 ± 0.4 | 56 |
23.85 | 0.1 ± 0.1 | 57 | 4.4 ± 0.5 | 43 | 0.2 ± 0.1 | 27 | 4.2 ± 0.4 | 73 | 0.1 ± 0.1 | 49 | 4.2 ± 0.4 | 51 |
17.7 | 0.2 ± 0.1 | 57 | 4.4 ± 0.4 | 43 | 0.2 ± 0.1 | 26 | 4.1 ± 0.4 | 74 | 0.1 ± 0.1 | 51 | 4.1 ± 0.4 | 49 |
11.9 | 0.2 ± 0.1 | 56 | 4.4 ± 0.4 | 44 | 0.2 ± 0.1 | 24 | 4.0 ± 0.4 | 76 | 0.2 ± 0.1 | 45 | 4.0 ± 0.4 | 55 |
6.19 | 0.2 ± 0.1 | 51 | 4.1 ± 0.4 | 49 | 0.3 ± 0.1 | 26 | 3.7 ± 0.4 | 74 | 0.2 ± 0.1 | 50 | 3.9 ± 0.4 | 50 |
(R,S)-KP-Trp | (S,R)-KP-Trp | (S,S)-KP-Trp | ||||
---|---|---|---|---|---|---|
ε | φfl | λem, nm | φfl | λem, nm | φfl | λem, nm |
36.8 | 0.0027 ± 0.0003 | 327 | 0.0043 ± 0.0004 | 328 | 0.0052 ± 0.0005 | 328 |
30.25 | 0.0025 ± 0.0003 | 325 | 0.0049 ± 0.0005 | 328 | 0.0061 ± 0.0006 | 328 |
23.85 | 0.0025 ± 0.0003 | 325 | 0.0049 ± 0.0005 | 328 | 0.0055 ± 0.0006 | 328 |
17.7 | 0.0026 ± 0.0003 | 326 | 0.0049 ± 0.0005 | 328 | 0.0052 ± 0.0005 | 328 |
11.9 | 0.0026 ± 0.0003 | 326 | 0.0054 ± 0.0005 | 326 | 0.0058 ± 0.0006 | 327 |
6.19 | 0.0026 ± 0.0003 | 325 | 0.0049 ± 0.0005 | 326 | 0.0052 ± 0.0005 | 325 |
kET | kRET | |
---|---|---|
(R,S)/(S,R) | 1 | 1.6 |
(S,S)/(R,S) | (4.7 ± 3.4) * | 0.5 |
(R,S) | (S,R) | (S,S) | |
---|---|---|---|
Distance, Å | 4.11 | 4.19 | 4.13 |
Interplane angle, ° | 32.3 | 56.3 | 30.1 |
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Ageeva, A.A.; Magin, I.M.; Doktorov, A.B.; Plyusnin, V.F.; Kuznetsova, P.S.; Stepanov, A.A.; Alekseev, A.A.; Polyakov, N.E.; Leshina, T.V. Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems. Int. J. Mol. Sci. 2021, 22, 6198. https://doi.org/10.3390/ijms22126198
Ageeva AA, Magin IM, Doktorov AB, Plyusnin VF, Kuznetsova PS, Stepanov AA, Alekseev AA, Polyakov NE, Leshina TV. Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems. International Journal of Molecular Sciences. 2021; 22(12):6198. https://doi.org/10.3390/ijms22126198
Chicago/Turabian StyleAgeeva, Aleksandra A., Ilya M. Magin, Alexander B. Doktorov, Victor F. Plyusnin, Polina S. Kuznetsova, Alexander A. Stepanov, Alexander A. Alekseev, Nikolay E. Polyakov, and Tatyana V. Leshina. 2021. "Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems" International Journal of Molecular Sciences 22, no. 12: 6198. https://doi.org/10.3390/ijms22126198