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NMR Spectroscopic Analysis on the Chiral Recognition of Noradrenaline by β-Cyclodextrin ( β-CD) and Carboxymethyl- β-cyclodextrin (CM- β-CD)
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  • NMR Spectroscopic Analysis on the Chiral Recognition of Noradrenaline by β-Cyclodextrin ( β-CD) and Carboxymethyl- β-cyclodextrin (CM- β-CD)
저자명
Lee. Sang-Hoo,Yi. Dong-Heui,Jung. Seung-Ho
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2004년|25권 2호|pp.216-220 (5 pages)
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

${eta}$-CD and CM- ${eta}$-CD as chiral NMR shift agents were used to resolve the enantiomers of noradrenaline (NA). The stoichiometry of each complex formed between the CDs and the enantiomers of NA was found to be 1 : 1 through the continuous variation plots. The binding constants (K) of the complexes were determined from $^1H$ NMR titration curves. This result indicated that both ${eta}$-CD and CM- ${eta}$-CD formed the complexes with the S(+)-NA more preferentially than its R(-)-enantiomer. The K values for the complexes with ${eta}$-CD ($K_{S(+)}$ = 537 $M^{-1}$ and $K_{R(-)}$ = 516 $M^{-1}$ was larger than those with CM- ${eta}$-CD ($K_{S(+)}$ = 435 $M^{-1}$ and $K_{R(-)}$ = 313 $M^{-1}$), however, enantioselectivity (${alpha}$) of S(+)- and R(-)-NA to CM- ${eta}$-CD ( ${alpha}$ = 1.38) was larger than that to ${eta}$-CD ( ${alpha}$ = 1.04), indicating that CM- ${eta}$-CD was the better chiral NMR solvating agents for the recognition of the enantiomers of NA. Two dimensional rotating frame nuclear Overhauser enhancement spectroscopy (ROESY) experiments were also performed to explain the binding properties in terms of spatial fitting of the NA molecule into the macrocyclic cavities.