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New 1H-pyrazole-containing polyamine receptors able to complex L-glutamate in water at physiological pH values

AuthorsMiranda, Carlos; Escarti, Francisco; Lamarque, Laurent; Yunta, María J. R.; Navarro, Pilar ; García-España, Enrique; Jimeno, M. Luisa
Issue Date2003
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 126 : 823-833 (2003)
AbstractThe interaction of the pyrazole-containing macrocyclic receptors 3,6,9,12,13,16,19,22,25,26- decaazatricyclo-[,14]-octacosa-1(27),11,14(28),24-tetraene 1[L1], 13,26-dibenzyl-3,6,9,12,13,16,- 19,22,25,26-decaazatricyclo-[,14]-octacosa-1(27),11,14(28),24-tetraene 2[L2], 3,9,12,13,16,22,- 25,26-octaazatricyclo-[,14]-octacosa-1(27),11,14(28),24-tetraene 3[L3], 6,19-dibenzyl-3,6,9,12,13,- 16,19,22,25,26-decaazatricyclo-[,14]-octacosa-1(27),11,14(28),24-tetraene 4[L4], 6,19-diphenethyl- 3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[,14]-octacosa-1(27),11,14(28),24-tetraene 5[L5], and 6,19-dioctyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[,14]-octacosa-1(27),11,14(28),24-tetraene 6[L6] with L-glutamate in aqueous solution has been studied by potentiometric techniques. The synthesis of receptors 3-6[L3-L6] is described for the first time. The potentiometric results show that 4[L4] containing benzyl groups in the central nitrogens of the polyamine side chains is the receptor displaying the larger interaction at pH 7.4 (Keff ) 2.04 104). The presence of phenethyl 5[L5] or octyl groups 6[L6] instead of benzyl groups 4[L4] in the central nitrogens of the chains produces a drastic decrease in the stability [Keff ) 3.51 102 (5), Keff ) 3.64 102 (6)]. The studies show the relevance of the central polyaminic nitrogen in the interaction with glutamate. 1[L1] and 2[L2] with secondary nitrogens in this position present significantly larger interactions than 3[L3], which lacks an amino group in the center of the chains. The NMR and modeling studies suggest the important contribution of hydrogen bonding and ð-cation interaction to adduct formation.
Publisher version (URL)http://dx.doi.org/10.1021/ja035671m
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