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A Tris‐Macrocycle with Proton Sponge Characteristics as Efficient Receptor for Inorganic Phosphate and Nucleotide Anions
Author(s) -
Bencini Andrea,
Biagini Silvia,
Giorgi Claudia,
Handel Henri,
Le Baccon Michel,
Mariani Palma,
Paoletti Piero,
Paoli Paola,
Rossi Patrizia,
Tripier Raphaël,
Valtancoli Barbara
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900770
Subject(s) - chemistry , cyclen , protonation , adduct , nucleotide , aqueous solution , potentiometric titration , hydrogen bond , phosphate , methylene , titration , proton affinity , cryptand , stereochemistry , inorganic chemistry , medicinal chemistry , organic chemistry , molecule , ion , biochemistry , gene
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 1 H and 31 P 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 .(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)