Abstract
The synthesis of new 'bridged' β-cyclodextrin (β-CD) 'dimers' 7-12 was successfully achieved by two one-pot reactions from β-CD (3) and 6A-azido-6A-deoxy-β-CD (4). The 'phosphine imine' reaction was shown to be a superior approach compared to the Mitsunobu reaction as coupling strategy for the preparation of these 'dimers'. NMR Data, along with molecular-modelling calculations, suggest a 'helical-like' arrangement for the phenanthro-line-diyl-linked 'dimer' derivative 9. Complexation properties of 9 were established by UV-VIS-spectrophotometric titration toward four metals. Among them CuII or EuIII ions were complexed selectively by 9, but no complexation occurred wish LaIII and ZnII. In addition a specific and interesing esterase activity toward the phosphodiester bond of bis(4-nitrophenyl) phosphate anion was found in the case of the CuIIcomplex of 9.
| Original language | English |
|---|---|
| Pages (from-to) | 632-645 |
| Number of pages | 14 |
| Journal | Helvetica Chimica Acta |
| Volume | 81 |
| Issue number | 4 |
| Publication status | Published - 1998 |
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Synthesis and Study of New β-Cyclodextrin 'Dimers' Having a Metal Coordination Center and Carboxamide or Urea Linkers. / Sallas, Florence; Marsura, Alain; Petot, Virginie; Pintér, I.; Kovács, J.; Jicsinszky, Laszlo.
In: Helvetica Chimica Acta, Vol. 81, No. 4, 1998, p. 632-645.Research output: Article
}
TY - JOUR
T1 - Synthesis and Study of New β-Cyclodextrin 'Dimers' Having a Metal Coordination Center and Carboxamide or Urea Linkers
AU - Sallas, Florence
AU - Marsura, Alain
AU - Petot, Virginie
AU - Pintér, I.
AU - Kovács, J.
AU - Jicsinszky, Laszlo
PY - 1998
Y1 - 1998
N2 - The synthesis of new 'bridged' β-cyclodextrin (β-CD) 'dimers' 7-12 was successfully achieved by two one-pot reactions from β-CD (3) and 6A-azido-6A-deoxy-β-CD (4). The 'phosphine imine' reaction was shown to be a superior approach compared to the Mitsunobu reaction as coupling strategy for the preparation of these 'dimers'. NMR Data, along with molecular-modelling calculations, suggest a 'helical-like' arrangement for the phenanthro-line-diyl-linked 'dimer' derivative 9. Complexation properties of 9 were established by UV-VIS-spectrophotometric titration toward four metals. Among them CuII or EuIII ions were complexed selectively by 9, but no complexation occurred wish LaIII and ZnII. In addition a specific and interesing esterase activity toward the phosphodiester bond of bis(4-nitrophenyl) phosphate anion was found in the case of the CuIIcomplex of 9.
AB - The synthesis of new 'bridged' β-cyclodextrin (β-CD) 'dimers' 7-12 was successfully achieved by two one-pot reactions from β-CD (3) and 6A-azido-6A-deoxy-β-CD (4). The 'phosphine imine' reaction was shown to be a superior approach compared to the Mitsunobu reaction as coupling strategy for the preparation of these 'dimers'. NMR Data, along with molecular-modelling calculations, suggest a 'helical-like' arrangement for the phenanthro-line-diyl-linked 'dimer' derivative 9. Complexation properties of 9 were established by UV-VIS-spectrophotometric titration toward four metals. Among them CuII or EuIII ions were complexed selectively by 9, but no complexation occurred wish LaIII and ZnII. In addition a specific and interesing esterase activity toward the phosphodiester bond of bis(4-nitrophenyl) phosphate anion was found in the case of the CuIIcomplex of 9.
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M3 - Article
AN - SCOPUS:0001249783
VL - 81
SP - 632
EP - 645
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
SN - 0018-019X
IS - 4
ER -