RT info:eu-repo/semantics/article
T1 The role of the transient atropisomerism and chirality of flurbiprofen unveiled by laser‐ablation rotational spectroscopy
A1 Verde, Andrés
A1 López Alonso, Juan Carlos
A1 Blanco Rodríguez, Susana
K1 Atropisomerism
K1 Chirality
K1 Flurbiprofen
K1 Rotational spectroscopy
K1 Laser ablation
K1 23 Química
AB The   combination   of   atropisomerism   and   chirality   in   flurbiprofen  is  shown  to  be  relevant  concerning  its  pharmacological  activity. The two most stable conformers of a total of eight theoretically predicted  for  each  R-  or  S-  flurbiprofen  enantiomers  have  been  isolated in the cooling conditions of a supersonic jet and structurally characterized   by   laser   ablation   Fourier   transform   microwave   spectroscopy.  The  detected  conformers,  whose  structure  is  mainly  defined by three dihedral angles, only differ in the sign of the phenyl torsion angle giving rise to Sa and Ra atropisomers. A comparison with the structures available for the R- and S- enantiomers complexed to COX   isoforms   reveals   that   the   enzymes   select   only   the   Saatropisomers, resulting in a diastereoisomer-specific recognition. The most stable gas phase conformer is exclusively selected when using the S-  enantiomer  while  the  second  is  recognized  only  for  the  R- enantiomer.  These  experimental  results  highlight  the  importance  of  atropisomerism in drug design.
PB Wiley
SN 0947-6539
YR 2023
FD 2023
LK https://uvadoc.uva.es/handle/10324/58887
UL https://uvadoc.uva.es/handle/10324/58887
LA eng
NO Chemistry – A European Journal, 2023,  e202300064
NO Producción Científica
DS UVaDOC
RD 06-ago-2024