TY - JOUR
T1 - NMR-based conformational analysis of perezone and analogues
AU - Zepeda, L. Gerardo
AU - Burgueño-Tapia, Eleuterio
AU - Pérez-Hernández, Nury
AU - Cuevas, Gabriel
AU - Joseph-Nathan, Pedro
PY - 2013/4
Y1 - 2013/4
N2 - Complete assignment of the 1H NMR chemical shift and coupling constant values of perezone (1), O-methylperezone (2) and 6-hydroxyperezone (3) was carried out by total-line-shape-fitting calculations using the PERCH iterative spectra analysis software (PERCH Solutions Ltd., Kuopio, Finland). The resulting simulated spectra for the three compounds showed strong similarity to their corresponding experimental spectra. Particularly, all vicinal, allylic and homoallylic coupling constant values for the side chain of the three compounds were very similar, thus revealing that the conformation of these three molecules in solution is indeed almost identical. This fact is in agreement with extended side chain conformations over folded chain conformations because 1, 2 and 3 undergo completely different intramolecular cycloaddition reactions. In addition, results of double pulsed field gradient spin echo NOESY 1D experiments performed on perezone (1) were unable to provide evidence for folded conformers.
AB - Complete assignment of the 1H NMR chemical shift and coupling constant values of perezone (1), O-methylperezone (2) and 6-hydroxyperezone (3) was carried out by total-line-shape-fitting calculations using the PERCH iterative spectra analysis software (PERCH Solutions Ltd., Kuopio, Finland). The resulting simulated spectra for the three compounds showed strong similarity to their corresponding experimental spectra. Particularly, all vicinal, allylic and homoallylic coupling constant values for the side chain of the three compounds were very similar, thus revealing that the conformation of these three molecules in solution is indeed almost identical. This fact is in agreement with extended side chain conformations over folded chain conformations because 1, 2 and 3 undergo completely different intramolecular cycloaddition reactions. In addition, results of double pulsed field gradient spin echo NOESY 1D experiments performed on perezone (1) were unable to provide evidence for folded conformers.
KW - NOE
KW - O-methylperezone
KW - hydroxyperezone
KW - iterative NMR spectral analysis
KW - perezone
KW - pipitzol
UR - http://www.scopus.com/inward/record.url?scp=84875267158&partnerID=8YFLogxK
U2 - 10.1002/mrc.3940
DO - 10.1002/mrc.3940
M3 - Artículo
SN - 0749-1581
VL - 51
SP - 245
EP - 250
JO - Magnetic Resonance in Chemistry
JF - Magnetic Resonance in Chemistry
IS - 4
ER -