European Journal of Organic Chemistry · 2005 · 14 citations · 32 references
Natural SciencesBiochemistryChemistryComputational ChemistryMolecular RecognitionSupramolecular ChemistryHydrogen Bonding In BiomoleculesLigand BindingMacromolecular AssemblyMacromolecular StructureMacromolecular Structure DeterminationProtein DimerizationDimerization MotifsHydrogen Bonding In Molecular RecognitionMolecular Recognition ElementsNucleic Acid Base PairingNucleobase IsomerizationNucleobase RecognitionStructural Basis Of DimerizationThermodynamics Of Dimerization
Abstract A triple hydrogen‐bonding module based on 6‐alkynyl‐2‐amino‐3 H ‐pyrimidin‐4‐one was developed such as for self‐dimerization and for nucleobase recognition processes. The strength of the module for the self‐dimerization was determined by NMR and fluorimetric analyses in chloroform (Δ G 298 = –22 to –23 kJ/mol). DFT calculations and X‐ray structure analysis showed that the self‐dimerization consists of the three‐point hydrogen‐bonding including two kinds of tautomers of the module in an ADD · DAA mode. Selective recognition of the module for a cytidine derivative was also observed, and the free energy change for the complexation (Δ G 298 = –31 kJ/mol) is one of the highest values among triple hydrogen‐bonded complexes so far reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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