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...

Descripción completa

Detalles Bibliográficos
Autores principales: 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.
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