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Chirality in Nature

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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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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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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Isomerism in Complexes
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Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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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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Quiralidad helicoidal de ingeniería en nanocanales de ciclodextrina coordinados por metales

Zhiyuan Jiang1, Zhi Chen2, Xiujun Yu2

  • 1Department of Chemistry, The University of Hong Kong, Hong Kong, Hong Kong SAR 999077, China.

Journal of the American Chemical Society
|February 18, 2025
PubMed
Resumen

Los investigadores crearon nuevos helicatos de iones de plata (Ag +) utilizando ligandos basados en ciclodextrina. Estos nanocanales artificiales exhiben geometría y helicidad controlables, allanando el camino para nanoestructuras avanzadas.

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Área de la Ciencia:

  • Química supramolecular
  • Nanotecnología
  • Química de coordinación

Sus antecedentes:

  • Los helicatos son cruciales en los sistemas biológicos (ADN, proteínas).
  • Las ciclodextrinas son prometedoras para construir estructuras helicoidales.
  • La falta de herramientas controlables dificulta la construcción de nanocanales helicoidales artificiales.

Objetivo del estudio:

  • Desarrollar nanocanales helicoidales artificiales con geometría y helicidad controlables.
  • Para utilizar ligandos derivados de ciclodextrina y iones de plata para el ensamblaje de nanocanales.
  • Para explorar la influencia de la geometría de coordinación del metal en la helicidad.

Principales métodos:

  • El ensamblaje de los nanocanales helicoidales Ag6L2 de los ligandos derivados de la alfa-ciclodextrina.
  • Química de coordinación que incluye grupos piridinales y cationes Ag+.
  • Modulación de la helicidad de los nanocanales mediante la alteración de los sustituyentes de los ligandos (grupos metilo).
  • Cálculos teóricos para apoyar los hallazgos experimentales.

Principales resultados:

  • Se han sintetizado con éxito nanocanales helicoidales Ag6L2 con helicidad M o P controlable.
  • La coordinación tetraédrica de Ag+ promueve la helicidad; la coordinación lineal la disminuye.
  • La modificación del ligando controla con precisión la geometría y la helicidad de los nanocanales.
  • Formación de una red coordinada 2D con teselación hexagonal.

Conclusiones:

  • Se ha demostrado el fácil montaje de nanocanales helicoidales sintonizables utilizando ligandos basados en ciclodextrina e iones de plata.
  • Se puede lograr un control preciso de la helicidad y la geometría de los nanocanales.
  • Los hallazgos ofrecen una nueva plataforma para diseñar nanoestructuras helicoidales avanzadas.