From Flexible to Constrained Tris(tetraamine) Ligands: Synthesis, Acid-Base Properties, and Structural Effect on the Coordination Process with Nucleotides
作者： Anne-Sophie Delépine , Raphaël Tripier , Michel Le Baccon , Henri Handel
关键词:
摘要: This work presents the synthesis and characterization of L2 L3, which formed with previously described ligand L1 a family three tris(tetraamine) ligands based on mesitylenyl spacer. The trimeric differ from one to other by nature their tetraamine moieties: triethylenetetraamine (L1), cyclen (L2), constrained (L3). impact rigidification structure L3 acid―base properties is investigated, behavior towards triphosphate (TriP), adenosine monophosphate (AMP), diphosphate (ADP), (ATP) anion receptors explored potentiometric investigations. To characterize understand driving forces implicated in supramolecular assemblies, results are supported 1 H 31 P NMR measurements performed over wide pH range. ATP appears as most complexed particular attention given comparison its inorganic analogue highlight contribution π-stacking interactions. Results unambiguously show various coordination scheme induced ligands.
sci-hub.se 参考文章(47)
Jean‐Marie Lehn, Supramolecular Chemistry: Concepts and Perspectives Malta II : Frontiers of Chemical Sciences 2 : Research and Education in the Middle East, Malta. ,(1995) , 10.1002/3527607439
Rapha�l Tripier, St�phanie Develay, Michel Le Baccon, Fran�oise Chuburu, Fran�ois Michaud, Henri Handel, Self-assembly route from a bis-aminal derivative to a new cyclam based macropentacycle New Journal of Chemistry. ,vol. 28, pp. 173- 176 ,(2004) , 10.1039/B310074J
K. Friedrici, Arsenmittel und Flugzeugbekämpfung Angewandte Chemie. ,vol. 40, pp. 487- 488 ,(1927) , 10.1002/ANGE.19270401703
Gary R. Weisman, Edward H. Wong, Daniel C. Hill, Mark E. Rogers, David P. Reed, Joseph C. Calabrese, Synthesis and transition-metal complexes of new cross-bridged tetraamine ligands Chemical Communications. pp. 947- 948 ,(1996) , 10.1039/CC9960000947
Anne-Sophie Delépine, Raphaël Tripier, Nathalie Le Bris, Hélène Bernard, Aurélien Honraedt, Henri Handel, ATP and triphosphate anions complexation by bis-linear tetraamines: Strong interactions at neutral pH Inorganica Chimica Acta. ,vol. 362, pp. 3829- 3834 ,(2009) , 10.1016/J.ICA.2009.05.003
Reed M. Izatt, James J. Christensen, J. Howard Rytting, Sites and thermodynamic quantities associated with proton and metal ion interaction with ribonucleic acid, deoxyribonucleic acid, and their constituent bases, nucleosides, and and nucleotides Chemical Reviews. ,vol. 71, pp. 439- 481 ,(1971) , 10.1021/CR60273A002
Burt G. Feuerstein, Nagarajan Pattabiraman, Laurence J Marton, Molecular mechanics of the interactions of spermine with DNA: DNA bending as a result of ligand binding Nucleic Acids Research. ,vol. 18, pp. 1271- 1282 ,(1990) , 10.1093/NAR/18.5.1271
Roger Phillips, Adenosine and the adenine nucleotides. Ionization, metal complex formation, and conformation in solution. Chemical Reviews. ,vol. 66, pp. 501- 527 ,(1966) , 10.1021/CR60243A002
Andrea Bencini, Silvia Biagini, Claudia Giorgi, Henri Handel, Michel Le Baccon, Palma Mariani, Piero Paoletti, Paola Paoli, Patrizia Rossi, Raphaël Tripier, Barbara Valtancoli, A Tris-Macrocycle with Proton Sponge Characteristics as Efficient Receptor for Inorganic Phosphate and Nucleotide Anions European Journal of Organic Chemistry. ,vol. 2009, pp. 5610- 5621 ,(2009) , 10.1002/EJOC.200900770
M. Ciampolini, N. Nardi, B. Valtancoli, M. Micheloni, Small aza cages as “fast proton sponges” and strong lithium binders Coordination Chemistry Reviews. ,vol. 120, pp. 223- 236 ,(1992) , 10.1016/0010-8545(92)80053-T