Access the full text.
Sign up today, get DeepDyve free for 14 days.
G.-Q. Lin, Q.-D. You, J. F. Cheng, G.-Q. Lin, Q.-D. You, J. F. Cheng (2011)
Chiral Drugs: Chemistry and Biological Action
M. Mäurer, H. Stegmann, W. Hiller, B. Müller (1992)
Stereoelectronic and Steric Effects in the Synthesis and Recognition of Diastereomeric Ethers by NMR and EPR SpectroscopyChemische Berichte, 125
J. Bernstein (2002)
Polymorphism in Molecular Crystals
Kohei Sato, Y. Itoh, T. Aida (2014)
Homochiral supramolecular polymerization of bowl-shaped chiral macrocycles in solutionChemical Science, 5
V. Khlestkin, Yurii Glasachev, A. Kokorin, R. Kostyanovsky (2004)
ESR study of stereochemistry in chiral nitroxide radical crystalsMendeleev Communications, 14
W. Schwarz, K.-M. Dangel, G. Jones, J. Bargon (1982)
CIDNP studies of photoinitated electron-transfer reactions. Sensitized isomerization of an electron acceptor norbornadieneJournal of the American Chemical Society, 104
K. Salikhov, Iu. Molin, A. Buchachenko, P. Atkins, G. Ribina, L. Yuzina (1984)
Spin polarization and magnetic effects in radical reactions
(2004)
Balón, Spectrochem
B. Gilbert, J. Larkin, R. Norman (1972)
Electron spin resonance studies. Part XXXIV. The use of the aci-anion from nitromethane as a spin trap for organic radicals in aqueous solutionJournal of The Chemical Society-perkin Transactions 1
Sergio Abad, U. Pischel, M. Miranda (2005)
Intramolecular electron transfer in diastereomeric naphthalene—amine dyads: a fluorescence and laser flash photolysis studyPhotochemical & Photobiological Sciences, 4
Kristýna Krasulová, M. Šiller, O. Holas, Z. Dvořák, P. Anzenbacher (2016)
Enantiospecific effects of chiral drugs on cytochrome P450 inhibition in vitroXenobiotica, 46
Hannah Kerr, Lorna Softley, Kuthuru Suresh, P. Hodgkinson, I. Evans (2017)
Structure and physicochemical characterization of a naproxen–picolinamide cocrystalActa Crystallographica. Section C, Structural Chemistry, 73
I. Magin, P. Purtov, A. Kruppa, T. Leshina (2005)
Peculiarities of magnetic and spin effects in a biradical/stable radical complex (three-spin system). Theory and comparison with experiment.The journal of physical chemistry. A, 109 33
M. Goez (1992)
Pseudo steady-state photo-CIDNP measurementsChemical Physics Letters, 188
P. Levkin, A. Kokorin, V. Schurig, R. Kostyanovsky (2006)
Solid-state ESR differentiation between racemate versus enantiomer.Chirality, 18 4
Nikita Dubinets, A. Safonov, Alexander Bagaturyants (2016)
Structures and Binding Energies of the Naphthalene Dimer in Its Ground and Excited States.The journal of physical chemistry. A, 120 17
Kelsey Duggan, D. Hermanson, Joél Musée, J. Prusakiewicz, Jami Scheib, B. Carter, Surajit Banerjee, John Oates, L. Marnett (2011)
(R)-Profens are substrate-selective inhibitors of endocannabinoid oxygenation by COX-2.Nature chemical biology, 7 11
I. Vayá, I. Andreu, M. Jiménez, M. Miranda (2014)
Photooxygenation mechanisms in naproxen–amino acid linked systemsPhotochemical & Photobiological Sciences, 13
D. Rychkov, S. Arkhipov, E. Boldyreva (2014)
Simple and efficient modifications of well known techniques for reliable growth of high-quality crystals of small bioorganic moleculesJournal of Applied Crystallography, 47
A. Doktorov, S. Mikhailov, P. Purtov (1992)
Theory of geminate recombination of radical pairs with instantaneously changing spin-Hamiltonian. I. General theory and kinematic approximationChemical Physics, 160
E. Khramtsova, Alexandra Ageeva, A. Stepanov, V. Plyusnin, T. Leshina (2016)
Photoinduced Electron Transfer in Dyads with (R)-/(S)-Naproxen and (S)-TryptophanZeitschrift für Physikalische Chemie, 231
F. Frank (1953)
On spontaneous asymmetric synthesis.Biochimica et biophysica acta, 11 4
E. Khramtsova, D. Sosnovsky, A. Ageeva, E. Nuin, M. Marín, P. Purtov, S. Borisevich, S. Khursan, Heinz Roth, M. Miranda, V. Plyusnin, T. Leshina (2016)
Impact of chirality on the photoinduced charge transfer in linked systems containing naproxen enantiomers.Physical chemistry chemical physics : PCCP, 18 18
M. Jiménez, U. Pischel, M. Miranda (2007)
Photoinduced processes in naproxen-based chiral dyadsJournal of Photochemistry and Photobiology C-photochemistry Reviews, 8
A. Gavezzotti (1994)
Are Crystal Structures PredictableAccounts of Chemical Research, 27
K. Soai, Tsuneomi Kawasaki, A. Matsumoto (2014)
The origins of homochirality examined by using asymmetric autocatalysis.Chemical record, 14 1
Y. Ishida, T. Aida (2002)
Homochiral supramolecular polymerization of an "S"-shaped chiral monomer: translation of optical purity into molecular weight distribution.Journal of the American Chemical Society, 124 47
R. Hegstrom, D. Kondepudi (1996)
Influence of static magnetic fields on chirally autocatalytic radical-pair reactionsChemical Physics Letters, 253
Panchao Yin, Zhi-ming Zhang, Hongjin Lv, Tao Li, Fadi Haso, L. Hu, Baofang Zhang, J. Bacsa, Yongge Wei, Yan-Qing Gao, Y. Hou, Yang-guang Li, C. Hill, E. Wang, Tianbo Liu (2015)
Chiral recognition and selection during the self-assembly process of protein-mimic macroanionsNature Communications, 6
L. Pejov (2001)
A gradient-corrected density functional study of indole self-association through N–H⋯π hydrogen bondingChemical Physics Letters, 339
A. Gavezzotti, G. Filippini (1994)
Geometry of the Intermolecular X-H.cntdot..cntdot..cntdot.Y (X, Y = N, O) Hydrogen Bond and the Calibration of Empirical Hydrogen-Bond PotentialsThe Journal of Physical Chemistry, 98
J. Aladekomo, J. Birks (1965)
‘Excimer’ fluorescence VII. Spectral studies of naphthalene and its derivativesProceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences, 284
Qian Shen, Lu Wang, Hui Zhou, Huidi Jiang, Lushan Yu, S. Zeng (2013)
Stereoselective binding of chiral drugs to plasma proteinsActa Pharmacologica Sinica, 34
G. Lin, Jiange Zhang, Jie Cheng (2011)
Overview of Chirality and Chiral Drugs
J. Hatton, R. Richards (1962)
Solvent effects in N.M.R. spectra of amide solutionsMolecular Physics, 5
Accepted Manuscript Chemistry -A European Journal This article is protected by copyright. All rights reserved
R. Kreilick, J. Becher, E. Ullman (1969)
Stable free radicals. V. Electron spin resonance studies of nitronylnitroxide radicals with asymmetric centersJournal of the American Chemical Society, 91
M. Mäurer, H. Stegmann (1990)
Chiral recognition of diastereomeric esters and acetals by EPR and NMR investigationsChemische Berichte, 123
N. Saprygina, O. Morozova, N. Gritsan, O. Fedorova, A. Yurkovskaya (2011)
1H CIDNP study of the kinetics and mechanism of the reversible photoinduced oxidation of tryptophyl-tryptophan dipeptide in aqueous solutionsRussian Chemical Bulletin, 60
P. Schuler, F. Schaber, H. Stegmann, E. Janzen (1999)
Recognition of chirality in nitroxides using EPR and ENDOR spectroscopyMagnetic Resonance in Chemistry, 37
G. Closs, R. Miller (1979)
Laser flash photolysis with NMR detection. Microsecond time-resolved CIDNP: separation of geminate and random-phase processesJournal of the American Chemical Society, 101
M. Muñoz, R. Ferrero, C. Carmona, M. Balón (2004)
Hydrogen bonding interactions between indole and benzenoid-pi-bases.Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 60 1-2
This work has shown spin selectivity in electron transfer (ET) of diastereomers of (R,S)‐naproxen‐(S)‐N‐methylpyrrolidine and (R,S)‐naproxen‐(S)‐tryptophan dyads. Photoinduced ET in these dyads is interesting because of the still unexplained phenomenon of stereoselectivity in the drug activity of enantiomers. The chemically induced dynamic nuclear polarization (CIDNP) enhancement coefficients of (R,S)‐diastereomers are double those of the (S,S)‐analogue. These facts are also interesting because spin effects are among the most sensitive, even to small changes in spin and molecular dynamics of paramagnetic particles. Therefore, CIDNP reflects the difference in magnetoresonance parameters (hyperfine interaction constants (HFIs), g‐factor difference) and lifetimes of the paramagnetic forms of (R,S)‐ and (S,S)‐diastereomers. The difference in HFI values for diastereomers has been confirmed by a comparison of CIDNP experimental enhancement coefficients with those calculated. Additionally, the dependence of the CIDNP enhancement coefficients on diastereomer concentration has been observed for the naproxen‐N‐methylpyrrolidine dyad. This has been explained by the participation of ET in homo‐(R,S‐R,S or S,S‐S,S) and hetero‐(R,S‐S,S) dimers of dyads. In this case, the effectivity of ET, and consequently, CIDNP, is supposed to be different for (R,S)‐ and (S,S)‐homodimers, heterodimers, and monomers. The possibility of dyad dimer formation has been demonstrated by using high‐resolution X‐ray and NMR spectroscopy techniques.
Chemistry - A European Journal – Wiley
Published: Dec 12, 2018
Keywords: ; ; ; ;
Read and print from thousands of top scholarly journals.
Already have an account? Log in
Bookmark this article. You can see your Bookmarks on your DeepDyve Library.
To save an article, log in first, or sign up for a DeepDyve account if you don’t already have one.
Copy and paste the desired citation format or use the link below to download a file formatted for EndNote
Access the full text.
Sign up today, get DeepDyve free for 14 days.
All DeepDyve websites use cookies to improve your online experience. They were placed on your computer when you launched this website. You can change your cookie settings through your browser.