Elucidating the behavior of an enzyme international dating for marriage
To learn more about the pivotal requirements for the catalytic activity of hexamer I, we became interested in the structurally closely related pyrogallolarene hexamer II.It self-assembles from six units of pyrogallolarene 2.The encapsulation of triethylamine (5a) in II is clearly evident in the H-NMR spectrum (ESI-Fig. The integral of the phenolic groups of II diminishes upon treatment with 5a, while a new broad peak emerges between 3 and 7 ppm.Careful integration (ESI-Schemes 1 and 2, Table 2†) reveals that it accounts for the diminished phenolic protons, as well as for the water signal, which is no longer visible as a separate peak.For the design of new artificial enzyme-like catalysts, it is of fundamental importance to understand the prerequisites for catalytic activity.We which self-assembles from six units of resorcinarene 1 and eight water molecules (Fig.Surprisingly, hexamer II displays a different encapsulation behavior compared to I in chloroform solution.It was reported that hexamer I encapsulates both tertiary amines as well as alkylammonium species, The high affinity of ammonium salts for I can be explained by strong cation–π interactions.
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The functional mimicking of natural enzymes has been a very fascinating but also challenging research topic for decades.
Several supramolecular structures have been identified that are able to catalyze reactions inside their enzyme-like pockets.
These observations are consistent with our previous findings for capsule I, and thus indicate the concomitant protonation of tertiary amines upon encapsulation in II.
The integrity of the hexameric encapsulation complex was confirmed by DOSY spectroscopy (ESI-Fig. Therefore, the formation of smaller (dimeric, or monomeric) pyrogallolarene–cation complexes observed in methanol solution can be excluded.
Search for elucidating the behavior of an enzyme:
The closely related, self-assembled resorcinarene and pyrogallolarene capsules display contrasting and puzzling encapsulation behaviors.