TY - JOUR
T1 - Design and Function of Supramolecular Recognition Systems Based on Guest-Targeting Probe-Modified Cyclodextrin Receptors for ATP
AU - Fujita, Kyohhei
AU - Fujiwara, Shoji
AU - Yamada, Tatsuru
AU - Tsuchido, Yuji
AU - Hashimoto, Takeshi
AU - Hayashita, Takashi
N1 - Funding Information:
This work was financially supported by a Grant-in-Aid for Scientific Research (C) (Grant No. 15K05548) from the Japan Society for the Promotion of Science (JSPS) and a Grant-in Aid for Scientific Research (A) (Grant No. 26248038) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan.
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2017/1/20
Y1 - 2017/1/20
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.6b02513
DO - 10.1021/acs.joc.6b02513
M3 - Article
C2 - 27997800
AN - SCOPUS:85026248193
SN - 0022-3263
VL - 82
SP - 976
EP - 981
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -