Cargando…
Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems
The study of the L- and D-amino acid properties in proteins and peptides has attracted considerable attention in recent years, as the replacement of even one L-amino acid by its D-analogue due to aging of the body is resulted in a number of pathological conditions, including Alzheimer’s and Parkinso...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8227724/ https://www.ncbi.nlm.nih.gov/pubmed/34201293 http://dx.doi.org/10.3390/ijms22126198 |
_version_ | 1783712590174617600 |
---|---|
author | Ageeva, Aleksandra A. Magin, Ilya M. Doktorov, Alexander B. Plyusnin, Victor F. Kuznetsova, Polina S. Stepanov, Alexander A. Alekseev, Alexander A. Polyakov, Nikolay E. Leshina, Tatyana V. |
author_facet | Ageeva, Aleksandra A. Magin, Ilya M. Doktorov, Alexander B. Plyusnin, Victor F. Kuznetsova, Polina S. Stepanov, Alexander A. Alekseev, Alexander A. Polyakov, Nikolay E. Leshina, Tatyana V. |
author_sort | Ageeva, Aleksandra A. |
collection | PubMed |
description | The study of the L- and D-amino acid properties in proteins and peptides has attracted considerable attention in recent years, as the replacement of even one L-amino acid by its D-analogue due to aging of the body is resulted in a number of pathological conditions, including Alzheimer’s and Parkinson’s diseases. A recent trend is using short model systems to study the peculiarities of proteins with D-amino acids. In this report, the comparison of the excited states quenching of L- and D-tryptophan (Trp) in a model donor–acceptor dyad with (R)- and (S)-ketoprofen (KP-Trp) was carried out by photochemically induced dynamic nuclear polarization (CIDNP) and fluorescence spectroscopy. Quenching of the Trp excited states, which occurs via two mechanisms: prevailing resonance energy transfer (RET) and electron transfer (ET), indeed demonstrates some peculiarities for all three studied configurations of the dyad: (R,S)-, (S,R)-, and (S,S)-. Thus, the ET efficiency is identical for (S,R)- and (R,S)-enantiomers, while RET differs by 1.6 times. For (S,S)-, the CIDNP coefficient is almost an order of magnitude greater than for (R,S)- and (S,R)-. To understand the source of this difference, hyperpolarization of (S,S)-and (R,S)- has been calculated using theory involving the electron dipole–dipole interaction in the secular equation. |
format | Online Article Text |
id | pubmed-8227724 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-82277242021-06-26 Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems Ageeva, Aleksandra A. Magin, Ilya M. Doktorov, Alexander B. Plyusnin, Victor F. Kuznetsova, Polina S. Stepanov, Alexander A. Alekseev, Alexander A. Polyakov, Nikolay E. Leshina, Tatyana V. Int J Mol Sci Article The study of the L- and D-amino acid properties in proteins and peptides has attracted considerable attention in recent years, as the replacement of even one L-amino acid by its D-analogue due to aging of the body is resulted in a number of pathological conditions, including Alzheimer’s and Parkinson’s diseases. A recent trend is using short model systems to study the peculiarities of proteins with D-amino acids. In this report, the comparison of the excited states quenching of L- and D-tryptophan (Trp) in a model donor–acceptor dyad with (R)- and (S)-ketoprofen (KP-Trp) was carried out by photochemically induced dynamic nuclear polarization (CIDNP) and fluorescence spectroscopy. Quenching of the Trp excited states, which occurs via two mechanisms: prevailing resonance energy transfer (RET) and electron transfer (ET), indeed demonstrates some peculiarities for all three studied configurations of the dyad: (R,S)-, (S,R)-, and (S,S)-. Thus, the ET efficiency is identical for (S,R)- and (R,S)-enantiomers, while RET differs by 1.6 times. For (S,S)-, the CIDNP coefficient is almost an order of magnitude greater than for (R,S)- and (S,R)-. To understand the source of this difference, hyperpolarization of (S,S)-and (R,S)- has been calculated using theory involving the electron dipole–dipole interaction in the secular equation. MDPI 2021-06-08 /pmc/articles/PMC8227724/ /pubmed/34201293 http://dx.doi.org/10.3390/ijms22126198 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Ageeva, Aleksandra A. Magin, Ilya M. Doktorov, Alexander B. Plyusnin, Victor F. Kuznetsova, Polina S. Stepanov, Alexander A. Alekseev, Alexander A. Polyakov, Nikolay E. Leshina, Tatyana V. Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems |
title | Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems |
title_full | Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems |
title_fullStr | Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems |
title_full_unstemmed | Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems |
title_short | Role of Chiral Configuration in the Photoinduced Interaction of D- and L-Tryptophan with Optical Isomers of Ketoprofen in Linked Systems |
title_sort | role of chiral configuration in the photoinduced interaction of d- and l-tryptophan with optical isomers of ketoprofen in linked systems |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8227724/ https://www.ncbi.nlm.nih.gov/pubmed/34201293 http://dx.doi.org/10.3390/ijms22126198 |
work_keys_str_mv | AT ageevaaleksandraa roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT maginilyam roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT doktorovalexanderb roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT plyusninvictorf roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT kuznetsovapolinas roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT stepanovalexandera roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT alekseevalexandera roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT polyakovnikolaye roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems AT leshinatatyanav roleofchiralconfigurationinthephotoinducedinteractionofdandltryptophanwithopticalisomersofketoprofeninlinkedsystems |