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(Ethylenediaminetetraacetic Acid)cerium(IV) [Ce IV (EDTA)] Complexes with Dual Hydrophobic Binding Sites as Highly Efficient Catalysts for the Hydrolysis of Phosphodiesters
Author(s) -
Yan JiaMing,
Atsumi Masato,
Yuan DeQi,
Fujita Kahee
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200205)85:5<1496::aid-hlca1496>3.0.co;2-2
Subject(s) - chemistry , ethylenediaminetetraacetic acid , cerium , linker , catalysis , hydrolysis , titration , metal ions in aqueous solution , combinatorial chemistry , metal , chelation , polymer chemistry , inorganic chemistry , organic chemistry , computer science , operating system
β ‐Cyclodextrin ( β ‐CD) derivatives 1 with an amino group at C(6), C(3), or C(2) were homogeneously linked together by an ethylenediaminetetraacetic acid (EDTA) bridge ( Scheme ). Coordination of the linker to metal ions and cooperation of the dual cavities of 3 in binding hydrophobic guests were properly demonstrated by NMR techniques and a fluorescence‐based titration method, respectively. The hydrolysis of bis(4‐nitrophenyl) phosphate (BNPP) in the presence of Ce IV complexes of β ‐CD dimers 3 was tens of millionfold faster than that in the absence of the Ce IV complexes. Hydrophobic binding of the β ‐CD cavities was estimated to contribute to the catalysis by a factor of up to 520, and the type of modified sugar unit and the bridging positions influenced this cooperation between the β ‐CD moieties and the catalytic metal center.