A Tris-Macrocycle with Proton Sponge Characteristics as Efficient Receptor for Inorganic Phosphate and Nucleotide Anions

被引：17

作者：

Bencini, Andrea ^{[1
]}

Biagini, Silvia ^{[1
]}

Giorgi, Claudia ^{[1
]}

Handel, Henri ^{[2
]}

Le Baccon, Michel ^{[2
]}

Mariani, Palma ^{[1
]}

Paoletti, Piero ^{[1
]}

Paoli, Paola ^{[3
]}

Rossi, Patrizia ^{[3
]}

Tripier, Raphael ^{[2
]}

Valtancoli, Barbara ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim, I-50019 Sesto Fiorentino, Italy

[2] Univ Bretagne Occidentale, CNRS, UMR 6521, F-29238 Brest 3, France

[3] Univ Florence, Dipartimento Energet Sergio Stecco, I-50139 Florence, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 32期

关键词：

Macrocycles; Anion binding; Nucleotides; Proton sponge; Molecular modeling; Thermodynamics; GUEST SUPRAMOLECULAR CHEMISTRY; VAN-DER-WAALS; MOLECULAR RECOGNITION; CRYSTAL-STRUCTURES; BINDING; ATP; NMR; COORDINATION; COMPLEXES; LIGANDS;

D O I：

10.1002/ejoc.200900770

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis, characterisation and proton-sponge behaviour of a new linear constrained tris-macrocycle (L), containing three cyclen (cyclen = 1,4,7,10-tetraazacyclododecane) reinforced macrocycles connected by two 2,6-pyridinediylbis(methylene) linkers, is reported. Protonated forms of L are efficient receptors for inorganic phosphate and nucleotide anions (ATP and ADP). The binding properties of L toward these substrates have been investigated in aqueous solution by means of potentiometric titrations, determining the stability constants of the adducts. The interaction mode was clarified by using H-1 and P-31 NMR measurements in aqueous solution and by means of molecular modelling calculations carried out on differently protonated species of L as well as on several nucleotide-receptor adducts. The stability of the adducts is mainly due to charge-charge and hydrogen bonding interactions between the polyphosphate chain of nucleotides and the ammonium groups of L. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：5610 / 5621

页数：12

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