Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Large Acceleration Effects of Mono-6-(alkylamino)-$\beta$-cyclodextrins on the Cleavage of p-Nitrophenyl $\alpha$-Methoxyphenylacetate

  • Kwanghee Koh (Department of Chemistry, Chungnam National University) ;
  • Byung-Kue Kang (Department of Chemistry, Chungnam National University)
  • Published : 1994.09.20
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Abstract

Kinetic studies of the deacylation reactions of p-and m-nitrophenyl esters of (R or S)-${\alpha}$ -methoxyphenylacetic acid were performed in ${\beta}$ -CD, mono-6-deoxy-6-[N-(2-aminoethyl)]amino-${\beta}$-CD (${\beta}$-CDen) and mono-6-deoxy-6-[N-(2-aminoethyl)-2-aminoethyl] amino-${\beta}$-CD (${\beta}$-CDdien) media. The binding constants (K) of the substrates to the hosts and the rate constants ($k_{\varphi}^{CD}$) for the complexed substrates were determined. $k_{\varphi}^{CD}$ values are highly dependent on the hosts and the substrates, whereas differences in K values among them are modest. The p-nitrophenyl esters show larger acceleration by -${\beta}$-CDen and -${\beta}$-CDdien than the corresponding m-isomers, while the m-isomers are more reactive than the p-isomers in -${\beta}$-CD media. This is taken as an indication that the amino groups attached to the primary side of -${\beta}$-CD participate in the deacylation reaction.

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References

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