Chiral Recognition of Thiaheterohelicenes by Alkyl β-D-Pyranoside Micelles.Influence of Extension of Helix

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Chiral recognition of alkyl β-D-pyranoside micelles toward[7]and[5]heterohelicenes possessing helical structures was investigated by ^1H-NMR and CD(circular dichroism)spectroscopy. In dodecyl maltopyranoside micellar solution, P and M enantiomers of tetrathia[7]heterohelicene(7TH), which have rigid and stable helixes, manifested different chemical shifts in their ^1H-NMR spectra due to differences in the diastereomeric interactions, implying that the micelles undergo stronger recognition toward the M enantiomer than the P enantiomer. On the other hand, in octyl glucopyranoside micellar solution, trithia[5]heterohelicene(5TH)and two kinds of its derivatives which are rapidly equilibrated between the enantiomers in solution, agve no distictly resolved ^1H^NMR peaks for either enantiomer even at a lowered temperature. However, these racemic[5]heterohelicenes in the micelles did develop induced CD absorptions owing to a displacement of the equilibrium, suggesting from the signs of their Cotton effects that the micelles prefer the M enantiomer to its antipode in conformity with the^1H-NMR results of 7TH.
公益社団法人日本薬学会の論文
2001-01-01