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231224s2013 xx |||||o 00| ||eng c |
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|a 10.1002/mrc.3940
|2 doi
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|a pubmed24n0751.xml
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|a eng
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|a Zepeda, L Gerardo
|e verfasserin
|4 aut
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|a NMR-based conformational analysis of perezone and analogues
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|c 2013
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
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|2 rdamedia
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|a ƒa Online-Ressource
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|a Date Completed 30.01.2014
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|a Date Revised 25.11.2016
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a Copyright © 2013 John Wiley & Sons, Ltd.
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|a Complete assignment of the (1)H 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
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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a Sesquiterpenes
|2 NLM
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|a perezone
|2 NLM
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|a L7YL69207Z
|2 NLM
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|a Burgueño-Tapia, Eleuterio
|e verfasserin
|4 aut
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|a Pérez-Hernández, Nury
|e verfasserin
|4 aut
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|a Cuevas, Gabriel
|e verfasserin
|4 aut
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|a Joseph-Nathan, Pedro
|e verfasserin
|4 aut
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 51(2013), 4 vom: 08. Apr., Seite 245-50
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|x 1097-458X
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|g volume:51
|g year:2013
|g number:4
|g day:08
|g month:04
|g pages:245-50
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|u http://dx.doi.org/10.1002/mrc.3940
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