The structure of the molecular complex between the chiral selector (+)1-(3-allylpropyl)-(5R,8S,10R)-N,N-diethyl-N'-[6-methyl ergolin-8-yl]urea, C23H33N4O, (allyl-terguride) and the HPLC more retained (S)-enantiomer of dansyl-tryptophan, C23H23N3O4S, has been determined. It is a part of the study on the chiral recognition mechanism of ergot alkaloids, when used in chiral stationary phases (CSPs) for the separation of racemic mixture of organic acids by liquid chromatographic methods. At the pH of crystallization conditions, which mimic those corresponding to the best enantiodiscriminative activity, each molecule of (S)-dansyl-tryptophan is locked to a molecule of allyl-terguride by hydrogen bonds and by C-H center dot center dot center dot pi edge-to-face interactions.
A selector/selectand molecular complex for the study of enantiodiscriminative processes
Sinibaldi M
2006
Abstract
The structure of the molecular complex between the chiral selector (+)1-(3-allylpropyl)-(5R,8S,10R)-N,N-diethyl-N'-[6-methyl ergolin-8-yl]urea, C23H33N4O, (allyl-terguride) and the HPLC more retained (S)-enantiomer of dansyl-tryptophan, C23H23N3O4S, has been determined. It is a part of the study on the chiral recognition mechanism of ergot alkaloids, when used in chiral stationary phases (CSPs) for the separation of racemic mixture of organic acids by liquid chromatographic methods. At the pH of crystallization conditions, which mimic those corresponding to the best enantiodiscriminative activity, each molecule of (S)-dansyl-tryptophan is locked to a molecule of allyl-terguride by hydrogen bonds and by C-H center dot center dot center dot pi edge-to-face interactions.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
