engleski

Aminopyridine bioconjugates in solution and solid state

Amino acids coupled to substituted benzoic acid derivatives often show interesting supramolecular interactions in solid state (e.g. self-recognition / discrimination in a dimer), although rarely investigated in solution. Such interactions have been applied in molecular separation and catalysis, as well as in crystal engineering. Since these systems are comprised of biological building blocks, it is important to elucidate their structure as model compounds in both solution and solid-state. Investigation of these systems could be beneficial for a better understanding of chiral induction in catalytic systems. Herein, we test the self-recognition properties of such systems by simultaneously introducing additional hydrogen bonding and metal coordination through 2-aminopyridine. Different pyridine amino acid derivatives with esters of 1, 3, 5-benzene tricarboxylic acid and Zn complexes thereof were synthesized and characterized by various analytical methods. The results indicate selective formation of ligand dimers in both solution and solid-state. Using all-atom molecular dynamics simulations for different amino acid ligands in acetonitrile, we reveal a complex interaction pattern in dimers and at the same time also provide a molecular level description of their formation.

amino acids ; bioconjugates ; supramolecular chemistry

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