Synthetic Multidentate Macrocyclic Compounds
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The resulting cations often form salts that are soluble in nonpolar solvents, and for this reason crown ethers are useful in phase transfer catalysis. The denticity of the polyether influences the affinity of the crown ether for various cations. For example, crown-6 has high affinity for potassium cation, crown-5 for sodium cation, and crown-4 for lithium cation. The high affinity of crown-6 for potassium ions contributes to its toxicity.
Crown ethers are not the only macrocyclic ligands that have affinity for the potassium cation.
Thermodynamics and Kinetics of Cation-Macrocycle Interaction
Ionophores such as valinomycin also display a marked preference for the potassium cation over other cations. In , Charles Pedersen , who was a chemist working at DuPont , discovered a simple method of synthesizing a crown ether when he was trying to prepare a complexing agent for divalent cations.
This linking defines a polydentate ligand that could partially envelop the cation and, by ionization of the phenolic hydroxyls, neutralize the bound dication. He was surprised to isolate a by-product that strongly complexed potassium cations. Citing earlier work on the dissolution of potassium in crown-4,   he realized that the cyclic polyethers represented a new class of complexing agents that were capable of binding alkali metal cations.
Crown ether - Wikipedia
He proceeded to report systematic studies of the synthesis and binding properties of crown ethers in a seminal series of papers. The fields of organic synthesis , phase transfer catalysts , and other emerging disciplines benefited from the discovery of crown ethers. Pedersen particularly popularized the dibenzo crown ethers. Pedersen shared the Nobel Prize in Chemistry for the discovery of the synthetic routes to, and binding properties of, crown ethers. Apart from its high affinity for potassium cations, crown-6 can also bind to protonated amines and form very stable complexes in both solution and the gas phase.
Some amino acids , such as lysine , contain a primary amine on their side chains.
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The preliminary antimicrobial activities are assessed by determining their MIC minimum inhibitory concentration and MBC minimum bactericidal concentration values. Moreover, the enhanced antimicrobial activities could be confirmed through a time-kill assay over 1. It is suggested that the enhanced antimicrobial activities from macrocycle [Zn 2 L] to [Zn 2 L OSO ] could be ascribed to the incorporation of two bioactive sites into one molecule in our case. It is noted that this effective post-modification from sulfur to sulfone after forming the macrocyclic complex is necessary because the phenolic hydroxyl and aldehyde units in the dialdehyde precursor are both sensitive to the oxidant.
More interestingly, the sulfone-functionalized Schiff-base macrocyclic complex with dual bioactive sites displays enhanced antimicrobial activities in contrast to the undecorated macrocycle Fig.
Considering the scarcity of flexible Schiff-base macrocyclic backbones with sulfur-containing bridges, the current study is believed to provide a practical approach to access multi-functional macrocyclic molecules by means of the post-modification strategy. Schematic illustration for the air-oxidation from sulfur to sulfone-bridged Schiff-base macrocyclic complexes with dual bioactive sites displaying enhanced antimicrobial activities.
Lee, J. Gokel, G. Xue, M. Jie, K. Macrocyclic Amphiphiles. Chen, G. Yang, H. Ogoshi, T. Descalzo, A.
The Synthesis and Ion Bindings of Synthetic Multidentate Macrocyclic Compounds.
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