RT info:eu-repo/semantics/article
T1 The nicotinic agonist cytisine: The role of the NH···N interaction
A1 Aguado Vesperinas, Raúl
A1 Mata, Santiago
A1 Sanz Novo, Miguel
A1 Alonso Alonso, Elena Rita
A1 León Ona, Iker
A1 Alonso Hernández, José Luis
K1 Agonists
K1 Agonistas
K1 Chemical structure
K1 Estructura química
K1 Molecular structure
K1 Estructura molecular
K1 Nicotine
K1 Nicotina
AB We report a detailed structural study of cytisine, an alkaloid used to help with smoking cessation, looking forward to unveiling its role as a nicotinic agonist. High-resolution rotational spectroscopy has allowed us to characterize two different conformers exhibiting axial and equatorial arrangements of the piperidinic NH group. Unexpectedly, the axial form has been found as the predominant configuration, in contrast to that observed for related molecules, such as piperidine. This anomalous behavior has been justified in terms of an intramolecular NH···N hydrogen bond. Moreover, this interaction justifies the overstabilization of the axial conformer over the equatorial one and is crucial for the mechanism of action of cytisine over the nicotinic receptor, further rationalizing its behavior as a nicotinic agonist.
PB American Chemical Society
SN 1948-7185
YR 2022
FD 2022
LK https://uvadoc.uva.es/handle/10324/56569
UL https://uvadoc.uva.es/handle/10324/56569
LA eng
NO Journal of Physical Chemistry Letters, 2022, vol. 13, p. 9991–9996
NO Producción Científica
DS UVaDOC
RD 25-dic-2024