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Prochirality02:05

Prochirality

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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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Chirality in Nature02:30

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 at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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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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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
12.1K
Chirality02:25

Chirality

30.4K
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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Updated: Feb 26, 2026

Synthesis and Structure Determination of &#181;-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
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Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

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Efecto de herencia quiral en el sistema de coensamblaje reactivo basado en cistina

Zhuoer Wang1, Changyu Chu1, Aiyou Hao1

  • 1School of Chemistry and Chemical Engineering, Shandong University, Jinan, PR China.

Nature communications
|February 24, 2026
PubMed
Resumen

Los investigadores desarrollaron reacciones eficientes en estado condensado en autoensamblajes utilizando derivados aromáticos de cistina. Esto permite la reorganización molecular controlada y las reacciones en cascada, lo que impacta las estructuras de nanoarquitectura y la expresión quiral.

Palabras clave:
cistinaautoensamblajereacciones en estado condensadoherencia quiralmateriales inteligentesquímica supramolecularquímica orgánica

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Área de la Ciencia:

  • Ciencia de Materiales
  • Química Supramolecular
  • Química Orgánica

Sus antecedentes:

  • Las reacciones químicas controladas son cruciales para el diseño de materiales inteligentes.
  • Las reacciones en estados condensados son típicamente menos eficientes que en solución debido a la difusión limitada y las colisiones moleculares.

Objetivo del estudio:

  • Investigar los efectos de templación en autoensamblajes que experimentan múltiples reacciones.
  • Lograr transformaciones químicas eficientes en el estado sólido o agregado.
  • Explorar la expresión y herencia quiral en evoluciones topoquímicas.

Principales métodos:

  • Se utilizó un derivado aromático de cistina para formar autoensamblajes.
  • Se indujo la escisión del enlace disulfuro y la posterior reorganización molecular utilizando un reductor.
  • Se incorporó una molécula invitada (pentafluoropiridina) para reacciones en cascada a través de interacciones π-hole/π.

Principales resultados:

  • Se logró la escisión cuantitativa del enlace disulfuro y la reorganización molecular en agregados.
  • Se demostró una reacción en cascada eficiente de dos pasos (reducción y sustitución nucleofílica) en el estado condensado.
  • Se observó la templación y herencia de la expresión quiral macroscópica y las actividades quiroópticas.

Conclusiones:

  • Se introdujo una nueva clase de reacciones eficientes en estados autoensamblados con control flexible de invitados.
  • Se desveló el efecto de herencia quiral en evoluciones topoquímicas dentro de sistemas autoensamblados.
  • Se destacó el potencial para diseñar materiales inteligentes avanzados a través de reacciones controladas en estado condensado.