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Chirality02:25

Chirality

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Biology is a natural science that studies life and living organisms, including their structure, function, development, interactions, evolution, distribution, and taxonomy. The field's scope is extensive and divided into several specialized disciplines, such as anatomy, physiology, ethology, genetics, and many more. All living things share a few key traits, including cellular organization, heritable genetic material and the ability to adapt/evolve, metabolism to regulate energy needs, the...
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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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A reversible chemical reaction represents a chemical process that proceeds in both forward (left to right) and reverse (right to left) directions. When the rates of the forward and reverse reactions are equal, the concentrations of the reactant and product species remain constant over time and the system is at equilibrium. A special double arrow is used to emphasize the reversible nature of the reaction. The relative concentrations of reactants and products in equilibrium systems vary greatly;...
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A Stimuli-Responsive Molecular Capsule with Switchable Dynamics, Chirality, and Encapsulation Characteristics.

Lei Zhiquan1, Han Xie1, Sarah E Border1

  • 1Department of Chemistry & Biochemistry , The Ohio State University , 100 West 18th Avenue , Columbus , Ohio 43210 , United States.

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|August 14, 2018
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This study introduces a novel molecular capsule capable of binding small guests. Protonation enhances its preorganization and binding affinity, demonstrating an allosteric effect for potential molecular machines.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Molecular capsules are investigated for their host-guest chemistry.
  • Controlling capsule dynamics and preorganization is crucial for recognition properties.

Purpose of the Study:

  • To prepare and characterize a novel molecular capsule (1) with a tris(2-pyridylmethyl)amine (TPA) lid.
  • To investigate the conformational dynamics and guest recognition of capsule 1 and its protonated form.
  • To explore the allosteric behavior and potential applications in molecular machines.

Main Methods:

  • Synthesis and characterization of molecular capsule 1.
  • Experimental methods: Variable temperature 1H NMR spectroscopy.
  • Theoretical methods: Molecular Mechanics (MM) and Density Functional Theory (DFT) calculations.

Main Results:

  • Capsule 1 exhibits poor preorganization with dynamic P-to-M stereoisomerization of the TPA lid (ΔG‡ < 8 kcal/mol).
  • Capsule 1 shows weak binding affinities for small guests (Ka < 7 M⁻¹).
  • Protonation of capsule 1 yields [1·H]-Cl, which is more preorganized and exhibits significantly enhanced guest binding affinities (Ka = 100-400 M⁻¹).
  • The protonated capsule demonstrates an induced-fit binding mechanism, involving axis elongation and pyridine ring twisting.
  • Deprotonation/reprotonation cycles are reversible, releasing and re-binding guests.

Conclusions:

  • Protonation induces significant changes in the capsule's structure, dynamics, and guest recognition properties.
  • The allosteric behavior of capsule 1 offers a unique platform for developing smart functional materials and molecular machines.
  • The study highlights the importance of preorganization and conformational dynamics in molecular recognition.