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Vibrational circular dichroism spectroscopy study of paroxetine and femoxetine precursors
Author(s) -
Urbanová Marie,
Setnička Vladimír,
Bouř Petr,
Navrátilová Hana,
Volka Karel
Publication year - 2002
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.10104
Subject(s) - vibrational circular dichroism , chemistry , circular dichroism , spectroscopy , intermolecular force , infrared spectroscopy , ab initio , spectral line , absorption spectroscopy , crystallography , computational chemistry , molecule , organic chemistry , physics , quantum mechanics , astronomy
The solution structures of (3R,4S)‐ and (3S,4R)‐ 4‐(4‐fluorophenyl)‐3‐hydroxylmethyl‐ 1‐methylpiperidine, which are intermediates in the synthesis of the two pharmaceuticals paroxetine and femoxetine, were studied by vibrational circular dichroism (VCD) spectroscopy. In addition, six derivatives with different substituents attached to the C3 atom were prepared and their VCD and absorption spectra discussed with the aid of ab initio simulations. The VCD spectra were found to be sensitive to the geometry changes. In addition, a subtle variation caused by intermolecular aggregation was apparent in the spectra. The VCD technique can be applied for structural analysis of chiral pharmaceuticals in solutions. © 2002 Wiley Periodicals, Inc. Biopolymers (Biospectroscopy) 67: 298–301, 2002