Home / Publications / NMR investigation of photoinduced chiral inversion in (R)/(S)-naproxen–(S)-tryptophan linked system

NMR investigation of photoinduced chiral inversion in (R)/(S)-naproxen–(S)-tryptophan linked system

Aleksandra Andreevna Ageeva 1
Aleksandra Andreevna Ageeva
, 
Simon V Babenko 1
Simon V Babenko
, 
Nikolay Eduardovich Polyakov 1
Nikolay Eduardovich Polyakov
, 
Tatyana Viktorovna Leshina 1
Tatyana Viktorovna Leshina
10.1016/j.mencom.2019.05.006
Published 2019-04-26
Communication , Volume 29, Issue 3, 260-262
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Ageeva A. A. et al. NMR investigation of photoinduced chiral inversion in (R)/(S)-naproxen–(S)-tryptophan linked system // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 260-262.
GOST all authors (up to 50) Copy
Ageeva A. A., Babenko S. V., Polyakov N. E., Leshina T. V. NMR investigation of photoinduced chiral inversion in (R)/(S)-naproxen–(S)-tryptophan linked system // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 260-262.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2019.05.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.006
TI - NMR investigation of photoinduced chiral inversion in (R)/(S)-naproxen–(S)-tryptophan linked system
T2 - Mendeleev Communications
AU - Ageeva, Aleksandra Andreevna
AU - Babenko, Simon V
AU - Polyakov, Nikolay Eduardovich
AU - Leshina, Tatyana Viktorovna
PY - 2019
DA - 2019/04/26
PB - Mendeleev Communications
SP - 260-262
IS - 3
VL - 29
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Ageeva,
author = {Aleksandra Andreevna Ageeva and Simon V Babenko and Nikolay Eduardovich Polyakov and Tatyana Viktorovna Leshina},
title = {NMR investigation of photoinduced chiral inversion in (R)/(S)-naproxen–(S)-tryptophan linked system},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.006},
number = {3},
pages = {260--262},
doi = {10.1016/j.mencom.2019.05.006}
}
MLA
Cite this
MLA Copy
Ageeva, Aleksandra Andreevna, et al. “NMR investigation of photoinduced chiral inversion in (R)/(S)-naproxen–(S)-tryptophan linked system.” Mendeleev Communications, vol. 29, no. 3, Apr. 2019, pp. 260-262. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.006.

Abstract

The inversion of the chiral centers in (R)/(S)-naproxen–(S)-tryptophan linked system under UV irradiation has been detected by the 1H NMR spectroscopy as an example of the (R,S)-diastereomer transformation into (S,S) analogue in an achiral environment.

References

1.
Chiral Inversion of Drugs: Coincidence or Principle?
Wsol V., Skalova L., Szotakova B.
Current Drug Metabolism, 2004
4.
10.1016/j.mencom.2019.05.006_bib0020
Chirality in Drug Design and Development, 2004
6.
10.1016/j.mencom.2019.05.006_bib0030
Iwakawa
Drug Metab. Dispos., 1991
7.
Chiral inversion of 2-arylpropionyl-CoA esters by human α-methylacyl-CoA racemase 1A (P504S)—a potential mechanism for the anti-cancer effects of ibuprofen
Woodman T.J., Wood P.J., Thompson A.S., Hutchings T.J., Steel G.R., Jiao P., Threadgill M.D., Lloyd M.D.
Chemical Communications, 2011
8.
α-Methylacyl-CoA racemase - an ‘obscure’ metabolic enzyme takes centre stage
Lloyd M.D., Darley D.J., Wierzbicki A.S., Threadgill M.D.
FEBS Journal, 2008
9.
Photoinduced Electron Transfer in Dyads with (R)-/(S)-Naproxen and (S)-Tryptophan
Khramtsova E.A., Ageeva A.A., Stepanov A.A., Plyusnin V.F., Leshina T.V.
Zeitschrift fur Physikalische Chemie, 2016
10.
Topological control in radical reactions of cholesterol in model dyads
Neshchadin D., Palumbo F., Sinicropi M.S., Andreu I., Gescheidt G., Miranda M.A.
Chemical Science, 2013
14.
New photodegradation pathways for Naproxen, a phototoxic non-steroidal anti-inflammatory drug
Boscá F., Miranda M.A., Vañó L., Vargas F.
Journal of Photochemistry and Photobiology A: Chemistry, 1990