Design and Function of Supramolecular Recognition Systems Based on Guest-Targeting Probe-Modified Cyclodextrin Receptors for ATP

Kyohhei Fujita, Shoji Fujiwara, Tatsuru Yamada, Yuji Tsuchido, Takeshi Hashimoto, Takashi Hayashita*

*この研究の対応する著者

研究成果: Article査読

24 被引用数 (Scopus)

抄録

In this study, we have developed a rational design strategy to obtain highly selective supramolecular recognition systems of cyclodextrins (CyDs) on the basis of the lock and key principle. We designed and synthesized dipicolylamine (dpa)-modified -CyD-Cu2+ complexes possessing an azobenzene unit (Cu·1-CyD) and examined how they recognized phosphoric acid derivatives in water. The results revealed that Cu·1-CyD recognized ATP with high selectivity over other phosphoric acid derivatives. The significant blue shift in the UV-vis spectra and 1H NMR analysis suggested that the selective ATP recognition was based on the multipoint interactions between the adenine moiety of ATP and both the CyD cavity and the azobenzene unit in addition to the recognition of phosphoric moieties by the Cu-dpa complex site. Our unique receptor made it capable of distinguishing ATP from AMP and ADP, revealing the discrimination of even a length of one phosphoric group. This study demonstrates that, compared to conventional recognition systems of CyDs, this multipoint recognition system confers a higher degree of selectivity for certain organic molecules, such as ATP, over their similar derivatives.

本文言語English
ページ(範囲)976-981
ページ数6
ジャーナルJournal of Organic Chemistry
82
2
DOI
出版ステータスPublished - 2017 1月 20
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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